120369-51-9

Basic information

• Product Name: (S)-tert-butyl 1-(benzylamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate
• Synonyms: (S)-tert-butyl 1-(benzylamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate
• CAS NO: 120369-51-9
• Molecular Weight: 338.471
• Mol File: 120369-51-9.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (S)-tert-butyl 1-(benzylamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-tert-butyl 1-(benzylamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate(120369-51-9)
• EPA Substance Registry System: (S)-tert-butyl 1-(benzylamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate(120369-51-9)

Safety Data

• Hazardous Substances Data: 120369-51-9(Hazardous Substances Data)

Upstream product

• 33900-24-2 N-(tert-butoxycarbonyl)-L-methionine methyl ester 
• 100-46-9 benzylamine 
• 2488-15-5 N-tert-butoxycarbonyl-L-methionine 

Downstream Products

• 92235-37-5 tert-butyl 1-benzyl-2-oxopyrrolidin-3-ylcarbamate 

Relevant articles and documents

Substituted Pyrrololactams via Ring Expansion of Spiro-2H-pyrroles from Intermolecular Alkyne-Isocyanide Click Reactions

The facile synthesis of 6- to 8-membered pyrrololactams has been developed using a ring expansion of spiro-2H-pyrroles, the products of intermolecular alkyne-isocyanide click reactions. The key to successful ring expansion of spiro-2H-pyrroles to pyrrololactams is the enforced orbital overlap between the internal alkene and the amide carbonyl group through the conformationally locked bicyclic structures. The newly disclosed α-isocyano lactams, substrates for click reactions, should find their utility in the synthesis of pharmaceutically important heterocyclic compounds.

Hafnium-catalyzed direct amide formation at room temperature

Herein, the first example of a metal-catalyzed protocol for direct amidation of nonactivated carboxylic acids at ambient temperature (26 °C) is presented. The mild reaction conditions give rise to high yields of a range of amides in reaction times as short as 90 min, employing a commercial hafnium complex, [Hf(Cp)2Cl2], as catalyst. Amino acids are transformed into their corresponding amides without racemization, and the catalyst displays full selectivity for the amidation of carboxylic acids over esters. Electronic properties of the carboxylic acids were found to have a strong influence on the rate of the amidation reaction, and the need for a balanced amount of molecular sieves was observed to be highly important for optimal reaction outcome.

Sodium methoxide: A simple but highly efficient catalyst for the direct amidation of esters

A simple NaOMe catalyst provides superior accessibility to a wide variety of functionalized amides including peptides through direct amination of esters in an atom-economical and environmentally benign way.