58177-77-8

Basic information

• Product Name: BOC-ALA-OTBU
• Synonyms: BOC-L-ALANINE T-BUTYL ESTER;BOC-ALA-OTBU;Boc-L-Ala-OtBu;N-Boc-L-alanine tert-butyl ester;(S)-tert-Butyl2-((tert-butoxycarbonyl)amino)propanoate
• CAS NO: 58177-77-8
• Molecular Formula: C₁₂H₂₃NO₄
• Molecular Weight: 245.32
• EINECS: 1533716-785-6
• Mol File: 58177-77-8.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BOC-ALA-OTBU(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-ALA-OTBU(58177-77-8)
• EPA Substance Registry System: BOC-ALA-OTBU(58177-77-8)

Safety Data

• Hazardous Substances Data: 58177-77-8(Hazardous Substances Data)

Usage

Description

BOC-ALA-OTBU, also known as N-(tert-Butoxycarbonyl)alanine tert-Butyl Ester, is a chemical compound that serves as a precursor in the synthesis of N-protected amino acid tert-Bu esters. It is characterized by the presence of a tert-butoxycarbonyl (BOC) group and a tert-butyl (OTBU) ester group, which protect the amino and carboxyl groups, respectively, during chemical reactions.

Uses

Used in Pharmaceutical Industry:
BOC-ALA-OTBU is used as a precursor in the synthesis of N-protected amino acid tert-Bu esters for the development of pharmaceutical compounds. The BOC and OTBU protecting groups allow for selective ester hydrolysis using ZnBr2 in DCM, enabling the controlled deprotection of the amino and carboxyl groups during the synthesis process. This selective hydrolysis is crucial for the preparation of complex peptide structures and the development of novel therapeutic agents.

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 21691-50-9 Ala-OtBu 
• 144347-37-5 (S)-2-tert-Butoxycarbonylamino-succinic acid 1-tert-butyl ester 4-(2-thioxo-2H-pyridin-1-yl) ester 
• 15761-38-3 L-N-Boc-Ala 
• 75-65-0 tert-butyl alcohol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 13404-22-3 tert-butyl L-alaninate hydrochloride 
• 875433-31-1 (2S)-N-[9-(4-bromophenyl)-9-fluorenyl]alanine tert-butyl ester 
• 875433-32-2 (2S)-N-(9-(4-morpholinophenyl)-9-fluorenyl)alanine tert-butyl ester 
• 34582-32-6 N-tert-butoxycarbonyl aspartic acid tert-butyl ester 
• 28875-17-4 (S)-N-(tert-butoxycarbonyl)alanine methyl ester 

Downstream Products

• 15761-38-3 L-N-Boc-Ala 
• 56-41-7 L-alanin 
• 13404-22-3 tert-butyl L-alaninate hydrochloride 

Relevant articles and documents

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μ-Oxo-Dinuclear-Iron(III)-Catalyzed O-Selective Acylation of Aliphatic and Aromatic Amino Alcohols and Transesterification of Tertiary Alcohols

A highly chemoselective and reactive μ-oxo-dinuclear iron(III) salen catalyst for transesterification was developed. The developed iron complex catalyzed acylation of aliphatic amino alcohols with nearly perfect O-selectivity, even when using activated esters, for which chemoselectivity is more difficult to control. In addition, O-selective transesterification of aromatic amino alcohols was achieved for the first time. The high activity of the iron complex enabled the use of sterically congested tertiary alcohols, including unprecedented tert-butanol.

9-(4-Bromophenyl)-9-fluorenyl as a safety-catch nitro gen protecting group

The 9-(4-bromophenyl)-9-fluorenyl (BrPhF) group has been developed as a novel safety-catch amine protection. This relatively acid-stable protecting group can be successfully activated by palladium-catalyzed cross-coupling reaction of the aryl bromide with morpholine and then cleaved effectively under mild conditions using dichloroacetic acid and triethylsilane. Complementary conditions are reported for selective removal of the BrPhF group in the presence of tert-butyl esters and carbamates as well as deprotection of tert-butyl esters and carbamates in the presence of BrPhF amines.