Water → Benzhydryl 7-(2-phenylacetamido)-3-allylthiomethyl-3-cephem-4-carboxylate

HRID 1494476Notes

Reaction equation

HRID 1494476 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:40](=[O:41])[N:13]3[C:14]([C:24]([O:26][CH:27]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[O:25])=[C:15]([CH2:19][S:20][CH2:21][CH:22]=[CH2:23])[CH2:16][S:17](=O)[C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)Cl.O>C(Cl)Cl>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:40](=[O:41])[N:13]3[C:14]([C:24]([O:26][CH:27]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:25])=[C:15]([CH2:19][S:20][CH2:21][CH:22]=[CH2:23])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24387Phosphorus trichlorideHCID 67712682Benzhydryl 7-(2-phenylacetamido)-3-allylthiomethyl-3-cephem-4-carboxylate-1-oxide

Product 1

HCID 67712927Benzhydryl 7-(2-phenylacetamido)-3-allylthiomethyl-3-cephem-4-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzhydryl 7-(2-phenylacetamido)-3-allylthiomethyl-3-cephem-4-carboxylate-1-oxide (26 g) in methylene chloride (500 ml) was added dropwise phosphorus trichloride (20 ml) at 5° C. with stirring, and the stirring was continued for an hour. The mixture was poured into a mixture of methylene chloride (200 ml) and water (400 ml), followed by separating out the organic layer, which was washed twice with an aqueous solution of sodium chloride (200 ml) and dried over anhydrous magnesium sulfate. After removal of the solvent, the residue was pulverized with diisopropyl ether to give benzhydryl 7-(2-phenylacetamido)-3-allylthiomethyl-3-cephem-4-carboxylate (22 g).

Workup

  1. waitthe stirring was continued for an hour
  2. customby separating out the organic layer, which
  3. washwas washed twice with an aqueous solution of sodium chloride (200 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removal of the solvent

Sources & evidence

ORD record
ord-a116428647124aa1ab56a2825c8d9923
Source dataset
uspto-grants-1991_06
Patent number
US05026695

Reaction notes

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