123052-80-2

Basic information

• Product Name: (2S,5S)-2-tert-Butyl-5-(3-chloro-benzyl)-3-methyl-4-oxo-imidazolidine-1-carboxylic acid tert-butyl ester
• CAS NO: 123052-80-2
• Molecular Weight: 380.915
• Mol File: 123052-80-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,5S)-2-tert-Butyl-5-(3-chloro-benzyl)-3-methyl-4-oxo-imidazolidine-1-carboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5S)-2-tert-Butyl-5-(3-chloro-benzyl)-3-methyl-4-oxo-imidazolidine-1-carboxylic acid tert-butyl ester(123052-80-2)
• EPA Substance Registry System: (2S,5S)-2-tert-Butyl-5-(3-chloro-benzyl)-3-methyl-4-oxo-imidazolidine-1-carboxylic acid tert-butyl ester(123052-80-2)

Safety Data

• Hazardous Substances Data: 123052-80-2(Hazardous Substances Data)

Upstream product

• 119838-38-9 (2S)-1-(tert-butyloxycarbonyl)-2-tert-butyl-3-methylimidazolidin-4-one 
• 766-80-3 1-bromomethyl-3-chlorobenzene 

Downstream Products

• 80126-51-8 (2S)-2-amino-3-(3-chlorophenyl)propanoic acid 

Relevant articles and documents

Synthesis of Nonproteinogenic (R)- or (S)-Amino Acids. - Analogues of Phenylalanine, Isotopically Labelled and Cyclic Amino Acids from tert-Butyl 2-(tert-Butyl)-3-methyl-4-oxo-1-imidazolidinecarboxylate (Boc-BMI)

The enantiomerically pure glycine derivatives (R)- and (S)-Boc-BMI, commercially available on a kg scale, are used as starting materials (Scheme 1) for the preparation of (i) open-chain amino acids such as α-deuterio amino acids (4,5), β-arylalanines (2), aspartic acid derivatives (6, 7a, 8), or ω-halo amino acids (7b,c, 12, 13, 16, 17, 19, 22), (ii) of α-aminocycloalkanecarboxylic acids (9, 11), and (iii) of heterocyclic α-amino acids (14, 15, 18, 20) containing azetidine, pyrrolidine, piperidine or perhydroazepine rings.Inversion by deprotonation/protonation ordeuteration allows to prepare either enantiomer of an amino acid from the same Boc-BMI enantiomer (Scheme 5).Effects of additives such as the cyclic urea DMPU, lithium salts, or secondeary amines upon the reactivity of lithium enolates are discussed and, in part, exploited.