Water → HCID 88600753, compound

HRID 2413817Notes

Reaction equation

HRID 2413817 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-fde341f0c60c42b5b164eb8bef7d1855
Source dataset
uspto-grants-1988_01
Patent number
US04719206

Reaction notes

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