Acetic Acid → HCID 131712104, compound

HRID 126901Notes

Reaction equation

[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:39])[C@@H:24]([NH:25][C:26](=[O:38])[C:27]([C:31]4[N:32]=[C:33]([NH2:37])[S:34][C:35]=4[Cl:36])=[N:28][O:29][CH3:30])[C@H:21]3[S:20][CH2:19][C:18]=2Cl)=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C>ClCCl.[Zn]>[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:39])[C@@H:24]([NH:25][C:26](=[O:38])[C:27]([C:31]4[N:32]=[C:33]([NH2:37])[S:34][C:35]=4[Cl:36])=[N:28][O:29][CH3:30])[C@H:21]3[S:20][CH2:19][CH:18]=2)=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of 7β-[2-(2-amino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid diphenylmethyl ester (180 mg) in dichloromethane (5 ml) are added zinc powder (120 mg) and acetic acid (1 ml), and the mixture is stirred at -10° C. for 10 minutes. The reaction mixture is filtered, poured into iced water and extracted with ethyl acetate. The extract solution is washed with aqueous sodium hydrogen carbonate solution and water, dried and concentrated. Conventional work-up of obtained residue affords 7β-[2-(2-amino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid diphenylmethyl ester. Similarly prepared are compounds of Table 1.

Workup

filtrationThe reaction mixture is filtered
additionpoured into iced water
extractionextracted with ethyl acetate
washThe extract solution is washed with aqueous sodium hydrogen carbonate solution and water
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-e9b1a409b547495d96981e6b32dab8e6
Source dataset: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04254119

Reaction notes

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