Hydrogen Peroxide → HCID 56616605, compound

HRID 638126Notes

Reaction equation

[Cl:1][CH2:2][C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:22][O:23][C:24]([C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=2)=[O:28])([CH3:26])[CH3:25])[C:12]([NH:14][C@H:15]2[C@@H:18]([C:19]#[N:20])[NH:17][C:16]2=[O:21])=[O:13])[N:10]=1)=[O:4].[OH:40]O.[OH-].[Na+]>CS(C)=O>[C:19]([C@H:18]1[NH:17][C:16](=[O:21])[C@H:15]1[NH:14][C:12](=[O:13])[C:11]([C:9]1[N:10]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][Cl:1])[S:7][CH:8]=1)=[N:22][O:23][C:24]([C:27]([O:29][CH2:30][C:31]1[CH:32]=[CH:33][C:34]([N+:37]([O-:39])=[O:38])=[CH:35][CH:36]=1)=[O:28])([CH3:26])[CH3:25])(=[O:40])[NH2:20]

Participants

Conditions

Temperature: 25 °C

Procedure

In 2 ml of dimethyl sulfoxide is dissolved 0.38 g of (3S,4S)-3-[2-(2-chloroacetamidothiazol-4-yl)-2-(1-p-nitrobenzyloxycarbonyl-1-methylethoxyimino)acetamido]-4-cyano-2-azetidinone and, following addition of 0.1 ml of 30% aqueous hydrogen peroxide and 0.1 ml of 1 N sodium hydroxide, the mixture is stirred at approx. 25° C. for 30 minutes. The reaction mixture is chromatographed on an XAD-II column (eluant: 30% ethanol) to give 0.12 of (3S,4S)-4-carbamoyl-3-[2-(2-chloroacetamidothiazol-4-yl)-2-(1-p-nitrobenzyloxycarbonyl-1-methylethoxyimino)acetamido]-2-azetidinone.

Workup

customThe reaction mixture is chromatographed on an XAD-II column (eluant: 30% ethanol)

Sources & evidence

ORD record: ord-f77f808c33f94d2895eaedf67ffb711d
Source dataset: uspto-grants-1985_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04560508

Reaction notes

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