Trifluoroacetic acid → 7beta-Formamido-3-chloromethyl-3-cephem-4carboxylic acid

HRID 1609657Notes

Reaction equation

[CH:1]([NH:3][C@@H:4]1[C:29](=[O:30])[N:6]2[C:7]([C:13]([O:15]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:14])=[C:8]([CH2:11][Cl:12])[CH2:9][S:10][C@H:5]12)=[O:2].FC(F)(F)C(O)=O.C(OC(C)C)(C)C.CCCCCC>ClCCl.C1(OC)C=CC=CC=1>[CH:1]([NH:3][C@@H:4]1[C:29](=[O:30])[N:6]2[C:7]([C:13]([OH:15])=[O:14])=[C:8]([CH2:11][Cl:12])[CH2:9][S:10][C@H:5]12)=[O:2]

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of benzhydryl 7β-formamido-3-chloromethyl-3-cephem-4-carboxylate (27.34 g) in a mixture of dichloromethane (137 ml) and anisole (27 ml) was added dropwise trifluoroacetic acid (54 ml) and the mixture was stirred at 5° C. for 1.2 hours. The mixture was added dropwise to a cooled mixture of diisopropyl ether (2 l) and hexane (2 l) and the resulting precipitates were collected by filtration, washed with a mixture of diisopropyl ether and hexane to give 7β-formamido-3-chloromethyl-3-cephem-4-carboxylic acid (14.03 g).

Workup

customthe resulting precipitates
filtrationwere collected by filtration
washwashed with a mixture of diisopropyl ether and hexane

Sources & evidence

ORD record: ord-d0e5f4f6c3b04201be6206322d88883e
Source dataset: uspto-grants-1995_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05401734

Reaction notes

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