Phosphorus trichloride → HCID 131714358, compound

HRID 464210Notes

Reaction equation

HRID 464210 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:42]1[N:43]=[C:44]([NH:47][CH:48]=[O:49])[S:45][CH:46]=1)[C:5]([NH:7][CH:8]1[C:40](=[O:41])[N:10]2[C:11]([C:24]([O:26][CH:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])=[C:12]([CH:16]=[CH:17][C:18]3[N:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH2:13][S:14](=O)[C@H:9]12)=[O:6].P(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:1][O:2][N:3]=[C:4]([C:42]1[N:43]=[C:44]([NH:47][CH:48]=[O:49])[S:45][CH:46]=1)[C:5]([NH:7][CH:8]1[C:40](=[O:41])[N:10]2[C:11]([C:24]([O:26][CH:27]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:25])=[C:12]([CH:16]=[CH:17][C:18]3[N:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

5

Reactant 3

HCID 24387Phosphorus trichlorideHCID 516892Sodium BicarbonateHCID 131714356HCID 131714356, compound

Product 1

HCID 131714358HCID 131714358, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[2-(3-pyridazinyl)vinyl]-3-cephem-4-carboxylate-1-oxide (syn isomer) (trans isomer) (1.8 g) in N,N-dimethylformamide (18 ml) was added phosphorus trichloride (0.45 ml) at -30° C. with stirring. The reaction mixture was stirred at -15° to -10° C. for 30 minutes and added dropwise to ice-water (100 ml). The suspension was adjusted to pH 7.5 with saturated aqueous sodium bicarbonate. The precipitate was collected by filtration, washed with water, dried under reduced pressure, and subjected to column chromatography on silica gel to give benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)-acetamido]-3-[2-(3-pyridazinyl)vinyl]-3-cephem-4-carboxylate (syn isomer) (trans isomer) (0.9 g).

Workup

  1. stirringThe reaction mixture was stirred at -15° to -10° C. for 30 minutes
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-eea8e4ea0c28423f90c266f1614de5d1
Source dataset
uspto-grants-1985_10
Patent number
US04546101

Reaction notes

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