Dimethylformamide → HCID 178480376, compound

HRID 1088035Notes

Reaction equation

HRID 1088035 reaction equation
[I-:1].[C:2]([O:6][C:7]([NH:9][C@@H:10]1[C:41](=[O:42])[N:12]2[C:13]([C:25]([O:27][CH:28]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])=[C:14]([CH2:18][N+:19]3[N:20]([CH3:24])[CH:21]=[CH:22][CH:23]=3)[CH2:15][S:16](=O)[C@H:11]12)=[O:8])([CH3:5])([CH3:4])[CH3:3].CN(C)C=O.P(Cl)(Cl)Cl>O>[I-:1].[C:2]([O:6][C:7]([NH:9][C@@H:10]1[C:41](=[O:42])[N:12]2[C:13]([C:25]([O:27][CH:28]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[O:26])=[C:14]([CH2:18][N+:19]3[N:20]([CH3:24])[CH:21]=[CH:22][CH:23]=3)[CH2:15][S:16][C@H:11]12)=[O:8])([CH3:5])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24387Phosphorus trichlorideHCID 178480377HCID 178480377, compound

Product 1

HCID 178480376HCID 178480376, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of benzhydryl 7β-tert-butoxycarbonylamino-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate 1-oxide iodide (20 g) and N,N-dimethylformamide (100 ml) was stirred at -35° C. Phosphorus trichloride (7.8 g) was added thereto and stirred for 10 minutes at the same temperature. The reaction mixture was added to water (600 ml). The precipitates were collected by filtration and washed with water to give benzhydryl 7β-tertbutoxycarbonylamino-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate iodide (15.4 g).

Workup

  1. filtrationThe precipitates were collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-97f60ad51eca4aaa8b88872c19b599b2
Source dataset
uspto-grants-1990_10
Patent number
US04960766

Reaction notes

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