Water → Benzhydryl 3-fluoromethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate

HRID 1605398Notes

Reaction equation

HRID 1605398 reaction equation
[F:1][CH2:2][C:3]1[CH2:4][S:5](=O)[C@@H:6]2[CH:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C:25](=[O:36])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].Cl[Sn]Cl.C(Cl)(=O)C.O>CC#N.CN(C)C=O>[F:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[CH:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C:25](=[O:36])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10]

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 24479Stannous ChlorideHCID 68131350Benzhydryl 3-fluoromethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate-1-oxide

Product 1

HCID 68132852Benzhydryl 3-fluoromethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2.08 g (3.7 mmole) of benzhydryl 3-fluoromethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate-1-oxide in 15 ml CH3CN and 6 ml DMF (dimethylformamide) at 0° is added 0.765 g (4.04 mmole) of anhydrous SnCl2 and 1.21 g (15.4 mmole) of acetyl chloride and the resulting mixture is stirred at 0° for 1.0 hrs, then at 30° for 1.0 hour, and then poured into water and extracted with ethyl acetate. The ethyl acetate layer is washed with 3% HCl solution, 5% NaHCO3 solution, and water, and then dried (MgSO4) and stripped in vacuo to yield benzhydryl 3-fluoromethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate, which can be purified by the method outlined in 3 above.

Workup

  1. waitat 30° for 1.0 hour
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer is washed with 3% HCl solution, 5% NaHCO3 solution, and water
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-08abaaf1ebe448b68d5948eaa3a075d8
Source dataset
uspto-grants-1976_04
Patent number
US03950329

Reaction notes

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