864167-26-0

Basic information

• Product Name: benzyl (S)-1-((S)-2-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-ylcarbaMoyl)pyrrolidin-1-yl)-3,3-diMethyl-1-oxobutan-2-ylcarbaMate
• Synonyms: benzyl (S)-1-((S)-2-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-ylcarbaMoyl)pyrrolidin-1-yl)-3,3-diMethyl-1-oxobutan-2-ylcarbaMate;Benzyl (S)-1-((S)-2-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-ylcarbamoyl)-pyrrolidin-1-yl)-3,3
• CAS NO: 864167-26-0
• Molecular Formula: C₂₅H₃₅N₃O₇
• Molecular Weight: 489.5613
• Mol File: 864167-26-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: benzyl (S)-1-((S)-2-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-ylcarbaMoyl)pyrrolidin-1-yl)-3,3-diMethyl-1-oxobutan-2-ylcarbaMate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl (S)-1-((S)-2-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-ylcarbaMoyl)pyrrolidin-1-yl)-3,3-diMethyl-1-oxobutan-2-ylcarbaMate(864167-26-0)
• EPA Substance Registry System: benzyl (S)-1-((S)-2-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-ylcarbaMoyl)pyrrolidin-1-yl)-3,3-diMethyl-1-oxobutan-2-ylcarbaMate(864167-26-0)

Safety Data

• Hazardous Substances Data: 864167-26-0(Hazardous Substances Data)

Upstream product

• 62965-37-1 (S)-2-(((benzyloxy)carbonyl)amino)-3,3-dimethylbutanoic acid dicyclohexylammonium salt 
• 864167-16-8 (1S)-2-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-ylcarbamoyl)pyrrolidine-1-carboxylic acid benzyl ester 
• 62965-10-0 (S)-N-carbobenzoxy-tert-butylleucine 

Relevant articles and documents

Development of a novel Pd-catalyzed N-acyl vinylogous carbamate synthesis for the key intermediate of ICE inhibitor VX-765

(Chemical Equation Presented) A novel Pd-catalyzed coupling of Cbz-protected proline amide with 4-bromo-5-ethoxyfuran-2(5H)-one was developed for the synthesis of the P1-P2 unit (5) of VX-765. The process afforded quantitative coupling in the presence of water, providing a 1:1 mixture of 5 and its ethoxy epimer epi-5. Compound 5 was isolated as a single diastereomer via fractional crystallization, which was stereoselectively converted to 17 via hydrogenation, and subsequently transformed to VX-765. Nine examples of the Pd coupling are presented with yields ranging from 76-98%.

PROCESSES AND INTERMEDIATES

The invention relates to processes and compounds useful for producing modified aspartic acid derivatives, such as aspartic acid aldehyde moieties. Aspartic acid derivatives are useful for preparing caspase inhibitors and/or prodrugs thereof.