19317-09-0

Basic information

• Product Name: benzyl (4-bromo-3-oxo-1-phenylbutan-2-yl)carbamate
• CAS NO: 19317-09-0
• Molecular Formula: C₁₈H₁₈BrNO₃
• Molecular Weight: 376.2444
• Mol File: 19317-09-0.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 522.2°C at 760 mmHg
• Flash Point: 269.6°C
• Density: 1.383g/cm³
• Vapor Pressure: 5.28E-11mmHg at 25°C
• Refractive Index: 1.591
• CAS DataBase Reference: benzyl (4-bromo-3-oxo-1-phenylbutan-2-yl)carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl (4-bromo-3-oxo-1-phenylbutan-2-yl)carbamate(19317-09-0)
• EPA Substance Registry System: benzyl (4-bromo-3-oxo-1-phenylbutan-2-yl)carbamate(19317-09-0)

Safety Data

• Hazardous Substances Data: 19317-09-0(Hazardous Substances Data)

Upstream product

• 41518-17-6 Z-Phe-O-COO-isoBu 
• 1161-13-3 N-Cbz-L-Phe 
• 143601-45-0 (S)-tert-butyl 4-<(benzyloxycarbonyl)amino>-3-oxo-5-phenylpentanoate 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 109453-49-8 (C₈H₇O₂)(NHCHCOO)(CH₂C₆H₅)(CO₂C₂H₅) 
• 191226-91-2 4-benzyloxycarbonylamino-2-bromo-3-oxo-5-phenyl-pentanoic acid tert-butyl ester 
• 15196-02-8 (S)-3-[(benzyloxycarbonyl)amino]-1-diazo-4-phenyl-2-butanone 

Downstream Products

• 269085-42-9 2-phenyl-4-(1-(S)-benzyloxycarbonylamino-2-phenylethyl)-1H-imidazole 
• 120452-06-4 3(S)-(Benzyloxyformamido)-1-bromo-4-phenyl-2(S)-butanol 

Relevant articles and documents

Continuous flow synthesis of α-halo ketones: Essential building blocks of antiretroviral agents

The development of a continuous flow process for the multistep synthesis of α-halo ketones starting from N-protected amino acids is described. The obtained α-halo ketones are chiral building blocks for the synthesis of HIV protease inhibitors, such as atazanavir and darunavir. The synthesis starts with the formation of a mixed anhydride in a first tubular reactor. The anhydride is subsequently combined with anhydrous diazomethane in a tube-in-tube reactor. The tube-in-tube reactor consists of an inner tube, made from a gas-permeable, hydrophobic material, enclosed in a thick-walled, impermeable outer tube. Diazomethane is generated in the inner tube in an aqueous medium, and anhydrous diazomethane subsequently diffuses through the permeable membrane into the outer chamber. The α-diazo ketone is produced from the mixed anhydride and diazomethane in the outer chamber, and the resulting diazo ketone is finally converted to the halo ketone with anhydrous ethereal hydrogen halide. This method eliminates the need to store, transport, or handle diazomethane and produces α-halo ketone building blocks in a multistep system without racemization in excellent yields. A fully continuous process allowed the synthesis of 1.84 g of α-chloro ketone from the respective N-protected amino acid within ～4.5 h (87% yield).

Ultrasound mediated synthesis of 2-amino-1,3-selenazoles derived from Fmoc/Boc/Z-α-amino acids

A simple and efficient one-pot synthesis of Fmoc/Boc/Z-amino acid derived 2-amino-1,3-selenazoles by the condensation of Nα-urethane protected amino acid derived bromomethyl ketones with selenourea under the influence of ultrasound has been described. Insertion of 2-amino-1,3-selenazole moiety in the side chains of Asp and Glu has also been achieved following the similar protocol. ARKAT USA, Inc.

Chiral imidazole derivatives synthesis from enantiopure N-protected α-amino acids

A route to the preparation of enantiopure ligands based on a 2-phenylimidazol ring is described. The stereogenic centre is placed into the chain bonded to the fourth carbon of the imidazole ring. The synthesis starts from inexpensive and readily available