65983-35-9

Basic information

• Product Name: 3-(TERT-BUTOXYCARBONYLAMINO)PROPANAMIDE
• Synonyms: 3-(TERT-BUTOXYCARBONYLAMINO)PROPANAMIDE;CarbaMic acid, (3-aMino-3-oxopropyl)-, 1,1-diMethylethyl ester;tert-butyl 3-aMino-3-oxopropylcarbaMate;N-(3-Amino-3-oxopropyl)carbamic acid 1,1-dimethylethyl ester;(2-Carbamoyl-ethyl)-carbamic acid tert-butyl ester;N3-{[(2-Methyl-2-propanyl)oxy]carbonyl}-β-alaninamide;TERT-BUTYL 2-CARBAMOYLETHYLCARBAMATE
• CAS NO: 65983-35-9
• Molecular Formula: C₈H₁₆N₂O₃
• Molecular Weight: 188.22
• Mol File: 65983-35-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-(TERT-BUTOXYCARBONYLAMINO)PROPANAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(TERT-BUTOXYCARBONYLAMINO)PROPANAMIDE(65983-35-9)
• EPA Substance Registry System: 3-(TERT-BUTOXYCARBONYLAMINO)PROPANAMIDE(65983-35-9)

Safety Data

• Hazardous Substances Data: 65983-35-9(Hazardous Substances Data)

Usage

General Description

3-(tert-Butoxycarbonylamino)propanamide, also known as BOC-beta-Ala-NH2 or (3-(((tert-Butoxy)carbonyl)amino)propanamide, is a chemical compound important in various industrial applications. This substance is an amino acid derivative characterized by its tert-butoxycarbonylamino functional group. It is commonly used as a protective reagent in procedures involving peptide synthesis due to its ability to protect the amine functional group. The protective nature of the tert-butoxycarbonyl group allows for selective reactions to occur in multi-step synthetic sequences. The BOC group can be removed under acidic conditions, making it suitable for processes that require the production of amino acids.

Upstream product

• 3303-84-2 3-(tert-butyloxycarbonylamino)propionic acid 
• 88574-53-2 3-tert-butoxycarbonylamino-propionic acid ethyl ester 
• 4726-85-6 β-alaninamide 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 53588-95-7 3-<(tert-butoxycarbonyl)amino>propionitrile 
• 77152-97-7 3-<(tert-butoxycarbonyl)amino>propiothioamide 

Relevant articles and documents

A convenient synthesis of ethyl 3-aminopropanedithioate (β-alanine ethyl dithioester)

A five-step sequence allowing the preparation of ethyl 3- aminopropanedithioate from N-(Boc)-β-alanine via the key intermediate N- (Boc)-β-alaninethioacyl-N-phthalimide is described.

Nitrilase-catalyzed hydrolysis of 3-aminopropionitrile at high concentration with a tandem reaction strategy for shifting the reaction to β-alanine formation

Given the importance of β-alanine, the nitrilase BjNIT3397 from Bradyrhizobium japonicum strain USDA110 was examined toward the hydrolysis of 3-aminopropionitrile. It has been found that nitrilase BjNIT3397 effectively hydrolyzed 3-aminopropionitrile with substrate concentration up to 3 M (210 g/L) at the pH 7.3 and temperature 30°C. With the increase of substrate concentration from 0.6 to 3 M, 3-aminopropanamide was formed and its percentage in the products was increased up to 33%. In order to reduce the formation of 3-aminopropanamide, aspartate ammonia-lyase and fumaric acid were added into the reaction system to consume the byproduct ammonia. As expected, the reaction was shifted toward the formation of β-alanine, resulting in the decrease of 3-aminopropanamide from 33% to 3%. Therefore, a tandem reaction strategy was developed to effectively prevent the formation of 3-aminopropanamide. This might also offer a possibility of producing β-alanine and L-aspartic acid in one process.

A Convenient and General Method for the Preparation of tert-Butoxycarbonylaminoalkanenitriles and Their Conversion to Mono-tert-butoxycarbonylalkanediamines

A new method is described for the synthesis of tert-butoxycarbonylaminoalkanenitriles 3 by dehydration of the corresponding carboxamides 2 (prepared in two steps from aminoalkanoic acids) in the presence of trifluoroacetic anhydride and triethylamine.N-Boc-aminoalkanenitriles 3 are easily converted to mono-N-Boc-alkanediamines 4 under mild conditions avoiding the cleavage of the N-protective group.The monoprotected alkanediamines 4 are useful tools in affinity chromatography.