HCID 23388303, compound → HCID 23388298, compound

HRID 1839344Notes

Reaction equation

[OH:1][C@@H:2]([C@H:4]1[C:33](=[O:34])[N:6]2[C:7]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=3)=[O:21])=[C:8]([C:10]3[S:14][C:13]4=[C:15]([S:18][CH3:19])[N:16]=[CH:17][N:12]4[CH:11]=3)[CH2:9][C@H:5]12)[CH3:3].[OH:35]OS([O-])=O.[K+]>>[OH:1][C@@H:2]([C@H:4]1[C:33](=[O:34])[N:6]2[C:7]([C:20]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=3)=[O:21])=[C:8]([C:10]3[S:14][C:13]4=[C:15]([S:18]([CH3:19])=[O:35])[N:16]=[CH:17][N:12]4[CH:11]=3)[CH2:9][C@H:5]12)[CH3:3]

Participants

Reactant 2

HCID 23388303HCID 23388303, compound

HCID 23707502Potassium hydroxy sulfite

Product 1

HCID 23388298HCID 23388298, compoundYield 40.5%

Procedure

A reaction was carried out in the same manner as in Example 44-b), except that 639 mg of 4-nitrobenzyl (5R,6S)-6-((1R)-1-hydroxyethyl)-2-(7-methylthioimidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate and 1.57 g of oxone were used as the starting compounds. The reaction product was purified by column chromatography on silica gel (dichloromethane:methanol=20:1 to 10:1) to give 267 mg of 4-nitrobenzyl (5R,6S)-6-((1R)-1-hydroxyethyl)-2-(7-methanesulfinylimidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate (a Mixture of Diastereomers).

Workup

customThe reaction product was purified by column chromatography on silica gel (dichloromethane:methanol=20:1 to 10:1)

Sources & evidence

ORD record: ord-727beabf790a4efa94ca74d3887c8902
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06677331B2

Reaction notes

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