Journal of Organic Chemistry 2009-11-20

Efficient preparation of aminoxyacyl amides, aminoxy hybrid peptides, and alpha-aminoxy peptides.

Alan R Katritzky, Ilker Avan, Srinivasa R Tala

Index: J. Org. Chem. 74th ed.,, 8690-8694, (2009)

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Abstract

N-(Pg-alpha-aminoxy acids) 1a-g are converted to N-(Pg-alpha-aminoxyacyl)benzotriazoles 2a-g, which react under mild conditions with amines, alpha-amino acids/alpha-dipeptides, and alpha-aminoxy acids to give aminoxyacyl amides 3a-g, (3e+3e'), and (3g+3g'), aminoxy hybrid peptides 4a-h, (4a+4a'), 6a-d, 9a-e, (9a+9a'), and (9b+9b'), and alpha-aminoxy peptides 10a,b in good yields without racemization.

Structure	Name/CAS No.	Molecular Formula	Articles
	(S)-Benzyl 1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate CAS:769922-77-2	C₂₃H₂₀N₄O₃
	(S)-Benzyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)carbamate CAS:850232-59-6	C₂₅H₂₁N₅O₃
	Z-Ile-Bt CAS:1072442-07-9	C₂₀H₂₂N₄O₃
	Benzyl 2-(1H-benzo[d][1,2,3]triazol-1-yl)-2-oxoethylcarbamate CAS:173459-80-8	C₁₆H₁₄N₄O₃
	Fmoc-Gly-Bt CAS:1082989-49-8	C₂₃H₁₈N₄O₃
	Fmoc-Pro-Bt CAS:1155875-68-5	C₂₆H₂₂N₄O₃

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Efficient preparation of aminoxyacyl amides, aminoxy hybrid peptides, and alpha-aminoxy peptides.

Abstract

Related Compounds