Dimethylformamide → HCID 14277601, compound

HRID 223419Notes

Reaction equation

CN(C)C=O.NC(N)=S.[Cl-].[NH4+].[C:12]1([CH2:18][C:19]([NH:21][CH:22]2[C:47](=[O:48])[N:24]3[C:25]([C:31]([O:33][CH:34]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[O:32])=[C:26]([CH2:29]Cl)[CH2:27][S:28][C@H:23]23)=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O.[Zn]>[C:12]1([CH2:18][C:19]([NH:21][CH:22]2[C:47](=[O:48])[N:24]3[CH:25]([C:31]([O:33][CH:34]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)=[O:32])[C:26](=[CH2:29])[CH2:27][S:28][C@H:23]23)=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: -15 °C

Procedure

To N,N-dimethylformamide (20 ml) were added thiourea (0.76 g), zinc powder (0.5 g) and a solution of ammonium chloride (0.67 g) in water (3 ml). To the mixture was added benzhydryl 7-phenylacetamido-3-chloromethyl-3-cephem-4-carboxylate (2.67 g) under cooling to -15° C. with stirring, and the mixture was stirred for an hour at -15° to -10° C., and then filtered. To the filtrate were added ethyl acetate (100 ml) and water (100 ml), and the organic layer was separated therefrom. The organic layer was washed with water, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was pulverized with diisopropyl ether to give benzhydryl 7-phenylacetamido-3-methylenecepham-4-carboxylate (2.2 g).

Workup

stirringthe mixture was stirred for an hour at -15° to -10° C.
filtrationfiltered
additionTo the filtrate were added ethyl acetate (100 ml) and water (100 ml)
customthe organic layer was separated
washThe organic layer was washed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-923c6fad3e264f3799af96754fe924ad
Source dataset: uspto-grants-1982_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04354022

Reaction notes

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