Trifluoroacetic acid → 7-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid trifluoroacetate

HRID 1030048Notes

Reaction equation

[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7](=[N:38][O:39][CH3:40])[C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[C:14]([C:20]([O:22]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:21])=[C:15]([CH2:18][Cl:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1.[F:41][C:42]([F:47])([F:46])[C:43]([OH:45])=[O:44].C(OC(C)C)(C)C.CCCCCC>ClCCl.C1(OC)C=CC=CC=1>[F:41][C:42]([F:47])([F:46])[C:43]([OH:45])=[O:44].[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7](=[N:38][O:39][CH3:40])[C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[C:14]([C:20]([OH:22])=[O:21])=[C:15]([CH2:18][Cl:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate (syn isomer) (3 g) in dichloromethane (6 ml) and anisole (3 ml) was added dropwise trifluoroacetic acid (6 ml) at 0° C. The mixture was stirred at 0° C. for two hours. The mixture was poured into a chilled mixture of diisopropyl ether and n-hexane (1:1, V/V). The precipitates were collected by filtration and dried under reduced pressure to give 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid trifluoroacetate (syn isomer) (2.50 g).

Workup

filtrationThe precipitates were collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-62d4f8efd7e948dd8b4f947dfcd40c52
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05104866

Reaction notes

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