m-Chloroperbenzoic acid → HCID 131714356, compound

HRID 980980Notes

Reaction equation

HRID 980980 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:41]1[N:42]=[C:43]([NH:46][CH:47]=[O:48])[S:44][CH:45]=1)[C:5]([NH:7][CH:8]1[C:39](=[O:40])[N:10]2[CH:11]([C:23]([O:25][CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[C:12]([CH:15]=[CH:16][C:17]3[N:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:13][S:14][C@H:9]12)=[O:6].ClC1C=CC=C(C(OO)=[O:57])C=1>C(Cl)Cl>[CH3:1][O:2][N:3]=[C:4]([C:41]1[N:42]=[C:43]([NH:46][CH:47]=[O:48])[S:44][CH:45]=1)[C:5]([NH:7][CH:8]1[C:39](=[O:40])[N:10]2[C:11]([C:23]([O:25][CH:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[O:24])=[C:12]([CH:15]=[CH:16][C:17]3[N:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH2:13][S:14](=[O:57])[C@H:9]12)=[O:6]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 131714357HCID 131714357, compound

Product 1

HCID 131714356HCID 131714356, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[2-(3-pyridazinyl)vinyl]-2-cephem-4-carboxylate (syn isomer) (trans isomer) (2.1 g) in methylene chloride (40 ml) was added a solution of 70% m-chloroperbenzoic acid (0.87 g) in methylene chloride (20 ml) at -35° C. with stirring. The reaction mixture was stirred at the same temperature for 20 minutes. The resultant solution was washed with 5% aqueous sodium bicarbonate. The separated organic layer was concentrated under reduced pressure and the residue was triturated in diisopropyl ether to give benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[2-(3-pyridazinyl)vinyl]-3-cephem-4-carboxylate-1-oxide (syn isomer) (trans isomer) (1.85 g).

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 20 minutes
  2. washThe resultant solution was washed with 5% aqueous sodium bicarbonate
  3. concentrationThe separated organic layer was concentrated under reduced pressure
  4. customthe residue was triturated in diisopropyl ether

Sources & evidence

ORD record
ord-0c6c83c98791481f82e6aed468879ecc
Source dataset
uspto-grants-1987_01
Patent number
US04639448

Reaction notes

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