Trifluoroacetic acid → HCID 140345175, compound

HRID 1709368Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:24]/[O:25][C:26]([C:29]([O:31]C(C)(C)C)=[O:30])([CH3:28])[CH3:27])/[C:8]([NH:10][C@H:11]2[C@@H:14]([C:15]([O:17][CH3:18])=[O:16])[N:13]([S:19]([OH:22])(=[O:21])=[O:20])[C:12]2=[O:23])=[O:9])[N:6]=1.FC(F)(F)C(O)=O>>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:24]/[O:25][C:26]([C:29]([OH:31])=[O:30])([CH3:27])[CH3:28])/[C:8]([NH:10][C@H:11]2[C@@H:14]([C:15]([O:17][CH3:18])=[O:16])[N:13]([S:19]([OH:22])(=[O:21])=[O:20])[C:12]2=[O:23])=[O:9])[N:6]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 172920750HCID 172920750, compound

Product 1

HCID 140345175HCID 140345175, compoundYield 5.5%

Procedure

550 mg of rac-cis-3-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-(t-butoxycarbonyl)-1-methylethoxy]imino]acetamido]-4-methoxycarbonyl-2-oxo-1-azetidinesulphonic acid are added at room temperature to 5.5 ml of trifluoroacetic acid. After 45 minutes, the mixture is evaporated and the residue is purified by chromatography on reverse-phase silica gel using water/methanol (4:1). There are obtained 27 mg of pure rac-cis-3-[(Z)-2-(2-amino-4-thiazolyl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-4-methoxycarbonyl-2-oxo-1-azetidinesulphonic acid as an amorphous lyophilizate.

Workup

customthe mixture is evaporated
customthe residue is purified by chromatography on reverse-phase silica gel

Sources & evidence

ORD record: ord-9dbc496646e2449f897399979cba3f36
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04948898

Reaction notes

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