Carbon Tetrachloride → HCID 88625624, compound

HRID 64746Notes

Reaction equation

[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[CH:14]([C:20]([O:22][CH:23]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:21])[C:15]([CH:18]=O)=[CH:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C.[C:63]([Cl:67])(Cl)(Cl)[Cl:64]>CN(C)C(=O)C.[Zn]>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[CH:14]([C:20]([O:22][CH:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)=[O:21])[C:15]([CH:18]=[C:63]([Cl:67])[Cl:64])=[CH:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Zinc powder (78.4 g) was added to a solution of benzhydryl 7-phenylacetamido-3-formyl-2-cephem-4-carboxylate (102.4 g) and triphenylphosphine (367.2 g) in a mixture of carbon tetrachloride (800 ml) and N,N-dimethylacetamide (200 ml) at ambient temperature and the mixture was stirred at 60° C. for 30 minutes. After being cooled, the mixture was added to ethyl acetate (20 l) and the resulting precipitates were filtered off and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel to give benzhydryl 7-phenylacetamido-3-(2,2-dichlorovinyl)-2-cephem-4-carboxylate (15.26 g).

Workup

temperatureAfter being cooled
customthe resulting precipitates
filtrationwere filtered off
customthe filtrate was evaporated in vacuo
customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-9092723d01d4419a80ee0a3ffe1e3b4a
Source dataset: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04609730

Reaction notes

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