57699-55-5

Basic information

• Product Name: N-t-butoxycarbonyl-N'-4-hydroxybenzyl hydrazine
• Synonyms: N-t-butoxycarbonyl-N'-4-hydroxybenzyl hydrazine
• CAS NO: 57699-55-5
• Molecular Weight: 238.287
• Mol File: 57699-55-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N-t-butoxycarbonyl-N'-4-hydroxybenzyl hydrazine(CAS DataBase Reference)
• NIST Chemistry Reference: N-t-butoxycarbonyl-N'-4-hydroxybenzyl hydrazine(57699-55-5)
• EPA Substance Registry System: N-t-butoxycarbonyl-N'-4-hydroxybenzyl hydrazine(57699-55-5)

Safety Data

• Hazardous Substances Data: 57699-55-5(Hazardous Substances Data)

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 870-46-2 t-butoxycarbonylhydrazine 
• 57699-48-6 3-(4-Hydroxybenzyliden)-carbazinsaeure-tert-butylester 
• 57699-48-6 N-t-butoxycarbonyl-N'-4-hydroxybenzaldehyde hydrazone 
• 52211-82-2 4-hydroxylbenzaldehyde hydrazone 

Downstream Products

• 512835-55-1 N-t-butoxycarbonyl-azatyrosine ethyl ester 
• 934-53-2 cumenyl chloride 
• 161852-52-4 N'-((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-N'-(4-hydroxy-benzyl)-hydrazinecarboxylic acid tert-butyl ester 

Relevant articles and documents

The efficient synthesis of azaamino acids

An efficient method of synthesis of N-t-butoxycarbonyl-azaamino acid ethyl esters has been described. This method consisted of three stages including: hydrazone formation, its reduction and acylation with ethyl chloroformate. The second step - reduction of the hydrazones to the appropriate hydrazides - was the most challenging. Some reducing agents have been tested, though NaBH3CN was found to lead to the final products with the highest yields in relatively short time and even to allow the selective reduction of C-N bond in the presence of nitro group.

Aza-peptide analogs as potent human immunodeficiency virus type-1 protease inhibitors with oral bioavailability

A series of aza-peptide analogs with a (hydroxyethyl)hydrazine isostere has been synthesized as HIV-1 protease inhibitors using a simple synthetic scheme. Structure-activity studies based on the X-ray of a previously described inhibitor-enzyme complex led to potent inhibitors with antiviral activity in the low-nanomolar range. The S-configuration of the transition- state hydroxyl group was preferred in this series. Small modifications of the P2P3 and P2'P3' substituents had little effect on enzyme inhibition but greatly influenced the pharmacokinetic profile. As a result of these studies, the symmetrically acylated compound 8a and its close analog 24a bearing a methyl carbamate in P3 and an ethyl carbamate in P3' position were identified as potent inhibitors with plasma concentrations exceeding antiviral ED50 values 150-fold following oral application in mice.

Polypeptides. Part XIII. Preparation of alpha-aza-amino-acid (carbazic acid) derivatives and intermediates for the preparation of alpha-aza-peptides.

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