Methanol → HCID 178441693, compound

HRID 1361921Notes

Reaction equation

HRID 1361921 reaction equation
CO.[CH2:3]([C:7]1[N:8]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[C:47]3[N:51](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:50]=[N:49][N:48]=3)=[CH:37][CH:36]=2)[C:9]([C:13]([O:15][CH:16]([O:18][C:19](=[O:33])[CH2:20][CH2:21][CH2:22][C@@H:23]([O:29][N+:30]([O-:32])=[O:31])[CH2:24][O:25][N+:26]([O-:28])=[O:27])[CH3:17])=[O:14])=[C:10]([Cl:12])[N:11]=1)[CH2:4][CH2:5][CH3:6]>ClCCl>[CH2:3]([C:7]1[N:8]([CH2:34][C:35]2[CH:36]=[CH:37][C:38]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[C:47]3[NH:51][N:50]=[N:49][N:48]=3)=[CH:39][CH:40]=2)[C:9]([C:13]([O:15][CH:16]([O:18][C:19](=[O:33])[CH2:20][CH2:21][CH2:22][C@@H:23]([O:29][N+:30]([O-:32])=[O:31])[CH2:24][O:25][N+:26]([O-:28])=[O:27])[CH3:17])=[O:14])=[C:10]([Cl:12])[N:11]=1)[CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 887MethanolHCID 86622537HCID 86622537, compound

Product 1

HCID 178441693HCID 178441693, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A methanol (5 mL)/dichloromethane (5 mL) solution of 1-{[(5R)-5,6-bis(nitrooxy)hexanoyl]oxy}ethyl 2-butyl-4-chloro-1-{[2′-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylate (713 mg, 0.756 mmol) was heated by microwave irradiation (120° C., 10 minutes). Purification of the reaction mixture by reversed-phase mass-directed high-performance liquid chromatography afforded the title compound. Chromatography of the diastereomeric mixture over Chiralpak AD-H, eluting with methanol/carbon dioxide, afforded the separate diastereomers.

Workup

  1. customPurification of the reaction mixture by reversed-phase mass-directed high-performance liquid chromatography

Sources & evidence

ORD record
ord-7d57072e941a473f8e89b4c1e69030b0
Source dataset
uspto-grants-2011_02
Patent number
US07880014B2

Reaction notes

Loading…