m-Chloroperbenzoic acid → HCID 131712702, compound

HRID 434868Notes

Reaction equation

HRID 434868 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:42]1[N:43]=[C:44]([NH:47][CH:48]=[O:49])[S:45][CH:46]=1)[C:5]([NH:7][CH:8]1[C:40](=[O:41])[N:10]2[C:11]([C:24]([O:26][CH:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])=[C:12]([CH2:15][O:16][C:17]([N:19]3[CH:23]=[CH:22][N:21]=[CH:20]3)=[O:18])[CH2:13][S:14][C@H:9]12)=[O:6].ClC1C=CC=C(C(OO)=[O:58])C=1>O1CCCC1>[CH3:1][O:2][N:3]=[C:4]([C:42]1[N:43]=[C:44]([NH:47][CH:48]=[O:49])[S:45][CH:46]=1)[C:5]([NH:7][CH:8]1[C:40](=[O:41])[N:10]2[C:11]([C:24]([O:26][CH:27]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])=[C:12]([CH2:15][O:16][C:17]([N:19]3[CH:23]=[CH:22][N:21]=[CH:20]3)=[O:18])[CH2:13][S:14](=[O:58])[C@H:9]12)=[O:6]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 131712703HCID 131712703, compound

Product 1

HCID 131712702HCID 131712702, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-imidazolyl)carbonyloxymethyl-3-cephem-4-carboxylate (syn isomer) (13.5 g) in tetrahydrofuran (200 ml) was added m-chloroperbenzoic acid (5.8 g) with stirring under ice-cooling, followed by stirring for an hour at 5° C. The reaction mixture was evaporated and the residue was pulverized in diethyl ether, collected by filtration, washed with ethyl acetate and diethyl ether and then dried to give benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-imidazolyl)carbonyloxymethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) (11.0 g).

Workup

  1. temperaturecooling
  2. stirringby stirring for an hour at 5° C
  3. customThe reaction mixture was evaporated
  4. filtrationcollected by filtration
  5. washwashed with ethyl acetate and diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-1802ea8ff7e54d5b8c111d569ee42dc6
Source dataset
uspto-grants-1983_08
Patent number
US04399278

Reaction notes

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