m-Chloroperbenzoic acid → 1-[(2S,3R)-2-hydroxy-5-(2-(methylsulfinyl)phenyl)-3-pentyl]imidazole-4-carboxamide

HRID 1072057Notes

Reaction equation

[OH:1][C@H:2]([C@H:4]([N:15]1[CH:19]=[C:18]([C:20]([NH2:22])=[O:21])[N:17]=[CH:16]1)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13][CH3:14])[CH3:3].ClC1C=CC=C(C(OO)=[O:31])C=1>ClCCl>[OH:1][C@H:2]([C@H:4]([N:15]1[CH:19]=[C:18]([C:20]([NH2:22])=[O:21])[N:17]=[CH:16]1)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([CH3:14])=[O:31])[CH3:3]

Participants

Conditions

Temperature: 5 °C

Procedure

A mixture of 1-[(2S,3R)-2-hydroxy-5-(2-(methylthio)phenyl)-3-pentyl]imidazole-4-carboxamide (7.1 mg) and m-chloroperbenzoic acid (75%; 5.12 mg) in dichloromethane (1 ml) was stirred at 5° C. for 2 hours. The mixture was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (5:1) to give a colorless oil of 1-[(2S,3R)-2-hydroxy-5-(2-(methylsulfinyl)phenyl)-3-pentyl]imidazole-4-carboxamide (3) (5.4 mg).

Workup

customThe mixture was purified by column chromatography on silica gel
washeluting with a mixture of dichloromethane and methanol (5:1)

Sources & evidence

ORD record: ord-b1b2be3f01b24f118c10e778d8c7c8bf
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06908940B2

Reaction notes

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