Synthesis of the HIV-proteinase inhibitor saquinavir: a challenge for process research

W Göbring, S Gokbale, H Hilpert…

Index: Chimia, , vol. 50, # 11 p. 532 - 537

Full Text: HTML

Citation Number: 45

Abstract

... 534 CHIMIA 50 (1996) Nr. ... ed. Reestab]ishing of the optical purity required purification via the crystalline p- TsOH salt of the benzy lester 8 followed ... give enantiomerically pure 9. Formation of the tetrahydroamide 12 was accomplished by hydrogeno]ysis of the amide 11 which in ...

 Related Synthetic Route
L-Phenylalanine Structure

63-91-2

L-Phenylalanine

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

H-Tic-OH Structure

74163-81-8

H-Tic-OH

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

Z-Tic-OH Structure

79261-58-8

Z-Tic-OH

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

(S)-1,2,3,4-tetrahydroisoquinoline-3-carbonyl chloride Structure

1064005-84-0

(S)-1,2,3,4-tet...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

(S)-N-tert-Butyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide Structure

149182-72-9

(S)-N-tert-Buty...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

benzyl 3(S)-(t-butylcarbamoyl)-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate Structure

149182-71-8

benzyl 3(S)-(t-...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

(S)-2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoyl chloride Structure

32150-91-7

(S)-2-(1,3-diox...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

2(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane Structure

136465-80-0

2(S)-[2-phenyl-...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

N/A Structure

136465-82-2

N/A

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

N-Phthaloyl-L-phenylalanine Structure

5123-55-7

N-Phthaloyl-L-p...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

Methyl L-phenylalaninate Structure

2577-90-4

Methyl L-phenyl...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

(S)-METHYL 2-((METHOXYCARBONYL)AMINO)-3-PHENYLPROPANOATE Structure

41844-71-7

(S)-METHYL 2-((...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

METHYL (1S,2S)-1-BENZYL-3-CHLORO-2-HYDROXYPROPYLCARBAMATE Structure

176972-62-6

METHYL (1S,2S)-...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

(S)-(1-benzyl-3-chloro-2-oxopropyl)carbamic acid methyl ester Structure

176972-61-5

(S)-(1-benzyl-3...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

(4S,5S)-5-hydroxymethyl-4-phenylmethyloxazolidinone Structure

147976-16-7

(4S,5S)-5-hydro...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

(4S,5S)-4-benzyl-2-oxo-oxazolidine-5-carboxylic acid Structure

147976-18-9

(4S,5S)-4-benzy...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

(4S,5S)-4-benzyl-2-oxo-oxazolidine-5-carboxylic acid methyl ether Structure

162221-36-5

(4S,5S)-4-benzy...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

N/A Structure

161525-75-3

N/A

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

[(4S,5S)-4-Benzyl-2-oxo-1,3-oxazolidin-5-yl]methyl 4-nitrobenzenesulfonate Structure

162221-28-5

[(4S,5S)-4-Benz...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

(2S)-1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanal Structure

55722-86-6

(2S)-1-(1,3-dio...

~%

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

L-Phenylalanine Structure

63-91-2

L-Phenylalanine

~%

(S)-N-tert-Butyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide Structure

149182-72-9

(S)-N-tert-Buty...

H-Tic-OH Structure

74163-81-8

H-Tic-OH

~%

(S)-N-tert-Butyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide Structure

149182-72-9

(S)-N-tert-Buty...

benzyl 3(S)-(t-butylcarbamoyl)-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate Structure

149182-71-8

benzyl 3(S)-(t-...

~%

(S)-N-tert-Butyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide Structure

149182-72-9

(S)-N-tert-Buty...

Z-Tic-OH Structure

79261-58-8

Z-Tic-OH

~%

(S)-N-tert-Butyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide Structure

149182-72-9

(S)-N-tert-Buty...

tert-Butylamine Structure

75-64-9

tert-Butylamine

(S)-1,2,3,4-tetrahydroisoquinoline-3-carbonyl chloride Structure

1064005-84-0

(S)-1,2,3,4-tet...

~%

(S)-N-tert-Butyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide Structure

149182-72-9

(S)-N-tert-Buty...

L-Phenylalanine Structure

63-91-2

L-Phenylalanine

~%

Z-Tic-OH Structure

79261-58-8

Z-Tic-OH

N2-(2-Quinolinylcarbonyl)-L-asparagine Structure

136465-98-0

N2-(2-Quinoliny...

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

~%

Saquinavir Structure

127779-20-8

Saquinavir

N-(TERT-BUTYL)DECAHYDRO-3-ISOQUINOLINECARBOXAMIDE Structure

128019-40-9

N-(TERT-BUTYL)D...

~%

Saquinavir Structure

127779-20-8

Saquinavir

(S)-2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoyl chloride Structure

32150-91-7

(S)-2-(1,3-diox...

~%

Saquinavir Structure

127779-20-8

Saquinavir

2(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane Structure

136465-80-0

2(S)-[2-phenyl-...

~%

Saquinavir Structure

127779-20-8

Saquinavir

N/A Structure

136465-82-2

N/A

~%

Saquinavir Structure

127779-20-8

Saquinavir

N-tert-Butyldecahydro-2-(2(R)-hydroxy-4-phenyl-3(S)phthalimidobutyl)-(4aS,8aS)-isoquinoline-3(S)-carboxamide Structure

136465-78-6

N-tert-Butyldec...

~%

Saquinavir Structure

127779-20-8

Saquinavir

(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Structure

136522-17-3

(3S,4aS,8aS)-2-...

~%

Saquinavir Structure

127779-20-8

Saquinavir

benzyl N-[(2S)-1-[[(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]amino]-4-amino-1,4-dioxobutan-2-yl]carbamate Structure

136522-18-4

benzyl N-[(2S)-...

~%

Saquinavir Structure

127779-20-8

Saquinavir

L-Phenylalanine Structure

63-91-2

L-Phenylalanine

~%

Saquinavir Structure

127779-20-8

Saquinavir

H-Tic-OH Structure

74163-81-8

H-Tic-OH

~%

Saquinavir Structure

127779-20-8

Saquinavir

(S)-1,2,3,4-tetrahydroisoquinoline-3-carbonyl chloride Structure

1064005-84-0

(S)-1,2,3,4-tet...

~%

Saquinavir Structure

127779-20-8

Saquinavir

(S)-N-tert-Butyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide Structure

149182-72-9

(S)-N-tert-Buty...

~%

Saquinavir Structure

127779-20-8

Saquinavir

benzyl 3(S)-(t-butylcarbamoyl)-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate Structure

149182-71-8

benzyl 3(S)-(t-...

~%

Saquinavir Structure

127779-20-8

Saquinavir

N-Phthaloyl-L-phenylalanine Structure

5123-55-7

N-Phthaloyl-L-p...

~%

Saquinavir Structure

127779-20-8

Saquinavir

Quinoline-2-carboxylic acid Structure

93-10-7

Quinoline-2-car...

~%

N2-(2-Quinolinylcarbonyl)-L-asparagine Structure

136465-98-0

N2-(2-Quinoliny...

L-asparagine Structure

70-47-3

L-asparagine

QUINALDIC ACID SUCCINIMIDE ESTER Structure

136465-99-1

QUINALDIC ACID ...

~%

N2-(2-Quinolinylcarbonyl)-L-asparagine Structure

136465-98-0

N2-(2-Quinoliny...

Z-Tic-OH Structure

79261-58-8

Z-Tic-OH

~%

Saquinavir Structure

127779-20-8

Saquinavir

Methyl L-phenylalaninate Structure

2577-90-4

Methyl L-phenyl...

~%

Saquinavir Structure

127779-20-8

Saquinavir

(S)-METHYL 2-((METHOXYCARBONYL)AMINO)-3-PHENYLPROPANOATE Structure

41844-71-7

(S)-METHYL 2-((...

~%

Saquinavir Structure

127779-20-8

Saquinavir

METHYL (1S,2S)-1-BENZYL-3-CHLORO-2-HYDROXYPROPYLCARBAMATE Structure

176972-62-6

METHYL (1S,2S)-...

~%

Saquinavir Structure

127779-20-8

Saquinavir

(S)-(1-benzyl-3-chloro-2-oxopropyl)carbamic acid methyl ester Structure

176972-61-5

(S)-(1-benzyl-3...

~%

Saquinavir Structure

127779-20-8

Saquinavir

N/A Structure

178680-13-2

N/A

~%

Saquinavir Structure

127779-20-8

Saquinavir

(4S,5S)-5-hydroxymethyl-4-phenylmethyloxazolidinone Structure

147976-16-7

(4S,5S)-5-hydro...

~%

Saquinavir Structure

127779-20-8

Saquinavir

(4S,5S)-4-benzyl-2-oxo-oxazolidine-5-carboxylic acid Structure

147976-18-9

(4S,5S)-4-benzy...

~%

Saquinavir Structure

127779-20-8

Saquinavir

(4S,5S)-4-benzyl-2-oxo-oxazolidine-5-carboxylic acid methyl ether Structure

162221-36-5

(4S,5S)-4-benzy...

~%

Saquinavir Structure

127779-20-8

Saquinavir

N/A Structure

161525-75-3

N/A

~%

Saquinavir Structure

127779-20-8

Saquinavir

[(4S,5S)-4-Benzyl-2-oxo-1,3-oxazolidin-5-yl]methyl 4-nitrobenzenesulfonate Structure

162221-28-5

[(4S,5S)-4-Benz...

~%

Saquinavir Structure

127779-20-8

Saquinavir

(2S)-1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanal Structure

55722-86-6

(2S)-1-(1,3-dio...

~%

Saquinavir Structure

127779-20-8

Saquinavir

Quinoline-2-carboxylic acid Structure

93-10-7

Quinoline-2-car...

~%

Saquinavir Structure

127779-20-8

Saquinavir

QUINALDIC ACID SUCCINIMIDE ESTER Structure

136465-99-1

QUINALDIC ACID ...

~%

Saquinavir Structure

127779-20-8

Saquinavir

QUINALDIC ACID SUCCINIMIDE ESTER Structure

136465-99-1

QUINALDIC ACID ...

2-[3(S)-[(L-asparaginyl)-amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert-butyl-decahydro(4aS,8aS)-isoquinoline-3(S)-carboxamide Structure

137431-06-2

2-[3(S)-[(L-asp...

~%

Saquinavir Structure

127779-20-8

Saquinavir


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