Dimethylformamide → HCID 178480371, compound

HRID 1088063Notes

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, 5.3 g) 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-e98a08c4e0ff4987bcd9aa58adc19aa7
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04960766

Reaction notes

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