Trifluoroacetic acid → HCID 178476693, compound

HRID 992698Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:44]/[O:45][C:46](=[O:48])[CH3:47])/[C:8]([NH:10][C@@H:11]2[C:42](=[O:43])[N:13]3[C:14]([C:26]([O:28]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:27])=[C:15]([S:18][CH2:19][C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C1(OC)C=CC=CC=1.[F:57][C:58]([F:63])([F:62])[C:59]([OH:61])=[O:60]>ClCCl>[F:57][C:58]([F:63])([F:62])[C:59]([OH:61])=[O:60].[F:57][C:58]([F:63])([F:62])[C:59]([OH:61])=[O:60].[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:44]/[O:45][C:46](=[O:48])[CH3:47])/[C:8]([NH:10][C@@H:11]2[C:42](=[O:43])[N:13]3[C:14]([C:26]([OH:28])=[O:27])=[C:15]([S:18][CH2:19][C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of diphenylmethyl 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(acetoxyimino)acetamido]-3-[(3-pyridyl)methylthio]-3-cephem-4-carboxylate (3.32 g, 4.83 m mol) and anisole (3.3 ml) in dichloromethane (16.6 ml) was added trifluoroacetic acid (6.6 ml) at 5° C. The mixture was stirred at 5° C. for 1.5 hours. The reaction mixture was poured into IPE. The resulting precipitates were collected by filtration, washed with IPE, and dried in vacuo to give 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(acetoxyimino)acetamido]-3-[(3-pyridyl)methylthio]-3-cephem-4-carboxylic acid bis(trifluoroacetic acid) salt (3.88 g, 5.08 m mol).

Workup

additionThe reaction mixture was poured into IPE
customThe resulting precipitates
filtrationwere collected by filtration
washwashed with IPE
customdried in vacuo

Sources & evidence

ORD record: ord-3ff5f2eb9ddd4241929e3c31ad688336
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06468995B1

Reaction notes

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