m-Chloroperbenzoic acid → Benzhydryl 3-fluoromethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate-1-oxide

HRID 1605402Notes

Reaction equation

HRID 1605402 reaction equation
[F:1][CH2:2][C:3]1[CH:8]([C:9]([O:11][CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[N:7]2[C:25](=[O:36])[CH:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C@H:6]2[S:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:45])C=1>C(Cl)(Cl)Cl>[F:1][CH2:2][C:3]1[CH2:4][S:5](=[O:45])[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

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68132614HCID 68132614, compound

Product 1

HCID 68131350Benzhydryl 3-fluoromethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate-1-oxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

To a solution of 1.04 g of benzhydryl 3-fluoromethyl-7-(2-thienylacetamido)-2-cephem-4-carboxylate in 10 ml of CHCl3 at 0° is added dropwise a solution of 0.35 g of m-chloroperbenzoic acid in 5 ml of CHCl3. The solution is stirred at 0° for 2.5 hours, then diluted with CHCl3 and washed with NaHCO 3, the dried (MgSO4) and evaporated in vacuo. The residue is recrystallized from methanol to yield benzhydryl 3-fluoromethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate-1-oxide.

Workup

  1. washwashed with NaHCO 3
  2. dry with materialthe dried (MgSO4)
  3. customevaporated in vacuo
  4. customThe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-90a932f6b1114379af9a97dd68aae9b4
Source dataset
uspto-grants-1976_04
Patent number
US03950329

Reaction notes

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