158512-24-4

Basic information

• Product Name: N-[N,O-ISOPROPYLIDENE-(2R)-HYDROXY INDAN-(1S)-YL]-(2R)-BENZYL-(4S,5)-EPOXY PENTANAMIDE
• Synonyms: N-[N,O-ISOPROPYLIDENE-(2R)-HYDROXY INDAN-(1S)-YL]-(2R)-BENZYL-(4S,5)-EPOXY PENTANAMIDE;[3aS-[3[S*(R*)],3aα,8aα]]-3,3a,8,8a-Tetrahydro-2,2-diMethyl-3-[2-(oxiranylMethyl)-1-oxo-3-phenylpropyl]-2H-indeno[1,2-d]oxazole
• CAS NO: 158512-24-4
• Molecular Formula: C₂₄H₂₇NO₃
• Molecular Weight: 377.47608
• Mol File: 158512-24-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 558.7°C at 760 mmHg
• Flash Point: 291.7°C
• Appearance: /
• Density: 1.183g/cm³
• Vapor Pressure: 1.62E-12mmHg at 25°C
• Refractive Index: 1.588
• CAS DataBase Reference: N-[N,O-ISOPROPYLIDENE-(2R)-HYDROXY INDAN-(1S)-YL]-(2R)-BENZYL-(4S,5)-EPOXY PENTANAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-[N,O-ISOPROPYLIDENE-(2R)-HYDROXY INDAN-(1S)-YL]-(2R)-BENZYL-(4S,5)-EPOXY PENTANAMIDE(158512-24-4)
• EPA Substance Registry System: N-[N,O-ISOPROPYLIDENE-(2R)-HYDROXY INDAN-(1S)-YL]-(2R)-BENZYL-(4S,5)-EPOXY PENTANAMIDE(158512-24-4)

Safety Data

• Hazardous Substances Data: 158512-24-4(Hazardous Substances Data)

Usage

Uses

An intermediate in the synthesis of Indinavir.

InChI:InChI=1/C24H27NO3/c1-24(2)25(22-20-11-7-6-10-17(20)14-21(22)28-24)23(26)18(13-19-15-27-19)12-16-8-4-3-5-9-16/h3-11,18-19,21-22H,12-15H2,1-2H3/t18?,19?,21-,22+/m1/s1

Upstream product

• 67843-74-7 (S)-epichlorohydrin 
• 141018-37-3 (3aS,8aR)-2,2-dimethyl-3-(3-phenylpropanoyl)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazole 
• 158380-42-8 (2R,4S)-2-Benzyl-5-chloro-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-4-hydroxy-pentan-1-one 
• 165883-49-8 (2R,4S)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-4-hydroxy-5-iodo-pentan-1-one 
• 150323-06-1 (S)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-pent-4-en-1-one 
• 70987-78-9 (S)-Glycidyl tosylate 

Downstream Products

• 150378-17-9 indinavir 
• 150323-38-9 [14C]-N-Dealkyl Indinavir 
• 181869-09-0 (2R,4S)-2-Benzyl-5-(2-tert-butylsulfamoyl-phenyl)-4-hydroxy-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide 
• 181869-12-5 N-tert-Butyl-2-[(2S,4R)-2-hydroxy-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-benzamide 
• 181869-01-2 (2R,4S)-2-Benzyl-5-(2,4-dimethoxy-phenyl)-4-hydroxy-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide 
• 181869-06-7 (2R,4S)-2-Benzyl-4-hydroxy-5-(2-methylsulfanyl-phenyl)-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide 
• 181869-00-1 (2R,4S)-2-Benzyl-4-hydroxy-5-(2-methoxy-phenyl)-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide 
• 181868-99-5 (2R,4S)-2-Benzyl-4-hydroxy-5-(2-hydroxy-phenyl)-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide 
• 181868-98-4 (2R,4S)-2-Benzyl-4-hydroxy-5-phenyl-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide 

Relevant articles and documents

A highly diastereoselective electrochemical epoxidation

The electrochemical epoxidation of 3 gives the Merck HIV-protease inhibitor, Indinavir Sulfate, intermediate 1 in high yield and diastereoselectivity in an operationally simple procedure.

Diastereoselective Syn-epoxidation of 2-alkyl-4-enamides to epoxyamides: Synthesis of the Merck HIV-1 protease inhibitor epoxide intermediate

Reaction of 2-alkyl-4-enamides 2, 9-15 with NIS and aqueous sodium bicarbonate results in the diastereoselective formation of the corresponding iodohydrins 3, 16-22 with essentially no iodolactone by-product. This methodology has been successfully employe