Dimethylformamide → HCID 178480371, compound

HRID 1614089Notes

Reaction equation

[I-:1].[CH:2]1([O:7][N:8]=[C:9]([C:46]2[N:47]=[C:48]([NH:51][CH:52]=[O:53])[S:49][CH:50]=2)[C:10]([NH:12][C@@H:13]2[C:44](=[O:45])[N:15]3[C:16]([C:28]([O:30][CH:31]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[O:29])=[C:17]([CH2:21][N+:22]4[N:23]([CH3:27])[CH:24]=[CH:25][CH:26]=4)[CH2:18][S:19](=O)[C@H:14]23)=[O:11])[CH2:6][CH2:5][CH:4]=[CH:3]1.CN(C)C=O.P(Cl)(Cl)Cl>O>[I-:1].[CH:2]1([O:7][N:8]=[C:9]([C:46]2[N:47]=[C:48]([NH:51][CH:52]=[O:53])[S:49][CH:50]=2)[C:10]([NH:12][C@@H:13]2[C:44](=[O:45])[N:15]3[C:16]([C:28]([O:30][CH:31]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[O:29])=[C:17]([CH2:21][N+:22]4[N:23]([CH3:27])[CH:24]=[CH:25][CH:26]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[CH2:6][CH2:5][CH:4]=[CH:3]1

Participants

Conditions

Temperature: -33 °C

Procedure

A mixture of benzhydryl 7β-[2-(2-cyclopenten-1-yloxyimino)-2-(2-formamidothiazol-4-yl)acetamido]-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate 1-oxide iodide (syn isomer, 5.3g) and N,N-dimethylformamide (50 ml) was stirred at -33° C. and phosphorus trichloride (1.68 g) was added thereto with stirring. The reaction mixture was stirred for 10 minutes at the same temperature, and poured into water (400 ml). Precipitates were collected by filtration and washed with water to give benzhydryl 7β-[2-(2-cyclopenten-1-yloxyimino)-2-(2-formamidothiazol-4-yl)acetamido]-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate iodide (syn isomer, 4.95 g).

Workup

stirringwith stirring
stirringThe reaction mixture was stirred for 10 minutes at the same temperature
customPrecipitates
filtrationwere collected by filtration
washwashed with water

Sources & evidence

ORD record: ord-225fd257b34f404eb981cea616f25e31
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05194432

Reaction notes

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