Water → HCID 88600753, compound

HRID 1380978Notes

Reaction equation

HRID 1380978 reaction equation
[CH:1]([NH:3][CH:4]1[C:30](=[O:31])[N:6]2[C:7]([C:14]([O:16][CH:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])=[C:8]([C:12]#[CH:13])[CH2:9][S:10](=O)[C@H:5]12)=[O:2].P(Cl)(Cl)Cl.O.C(OCC)(=O)C>CN(C)C=O>[CH:1]([NH:3][CH:4]1[C:30](=[O:31])[N:6]2[C:7]([C:14]([O:16][CH:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:15])=[C:8]([C:12]#[CH:13])[CH2:9][S:10][C@H:5]12)=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24387Phosphorus trichlorideHCID 88601110HCID 88601110, compound

Product 1

HCID 88600753HCID 88600753, compoundYield 9.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of benzhydryl 7-formamido-3-ethynyl-3-cephem-4-carboxylate-1-oxide (12 g) in N,N-dimethylformamide (96 ml) was added phosphorus trichloride (0.48 ml) at -20° C. and the resultant mixture was stirred at -20° C. to -10° C. for 10 minutes. After water and ethyl acetate were added to the reaction mixture, the separated organic layer was washed with water and brine, dried over magnesium sulfate. The solution was evaporated in vacuo to give benzhydryl 7-formamido-3-ethynyl-3-cephem-4-carboxylate (1.15 g).

Workup

  1. washthe separated organic layer was washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-0de4c15ebe034978bd38ecf79c83a555
Source dataset
uspto-grants-1986_04
Patent number
US04584290

Reaction notes

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