Efficient syntheses of pyrofolic acid and pteroyl azide, reagents for the production of carboxyl-differentiated derivatives of folic acid

J Luo, MD Smith, DA Lantrip, S Wang…

Index: Luo, Jin; Smith, Michael D.; Lantrip, Douglas A.; Wang, Susan; Fuchs Journal of the American Chemical Society, 1997 , vol. 119, # 42 p. 10004 - 10013

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Citation Number: 67

Abstract

Reaction of folic acid (1) with excess trifluoroacetic anhydride provides access to both the previously unknown N 10-(trifluoroacetyl) pyrofolic acid (8) and pyrofolic acid (9). Reaction of either of these materials with hydrazine selectively affords pteroyl hydrazide (13), which may be oxidized to pteroyl azide (27) on a large scale (62% overall from 1 without the need for chromatography). Treatment of 27 with differentially protected glutamates provides a ...