m-Chloroperbenzoic acid → HCID 70505391, compound

HRID 1463138Notes

Reaction equation

HRID 1463138 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH2:17][C:18]([NH:20][CH:21]1[C:53](=[O:54])[N:23]2[CH:24]([C:37]([O:39][CH:40]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:38])[C:25]([CH2:29][S:30][C:31]3[N:35]([CH3:36])[N:34]=[N:33][N:32]=3)=[C:26]([CH3:28])[S:27][C@H:22]12)=[O:19]>C(Cl)Cl>[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH2:17][C:18]([NH:20][CH:21]1[C:53](=[O:54])[N:23]2[C:24]([C:37]([O:39][CH:40]([C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)=[O:38])=[C:25]([CH2:29][S:30][C:31]3[N:35]([CH3:36])[N:34]=[N:33][N:32]=3)[C@@H:26]([CH3:28])[S:27](=[O:9])[C@H:22]12)=[O:19]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70504654HCID 70504654, compound

Product 1

HCID 70505391HCID 70505391, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 217 mg quantity of m-chloroperbenzoic acid was added to a solution of 662 mg of diphenylmethyl 7-(2-thienylacetamido)-2-methyl-3-(1-methyl-1H-tetrazol-5-yl)thiomethylceph-2-em-4-carboxylate in 30 ml of CH2Cl2 at -10° C., and the mixture was stirred at the same temperature for 1 hour. The reaction solution was washed with 10% Na2S2O3 solution and with saturated aqueous NaCl solution, and dried over MgSO4 to distill off the CH2Cl2 under reduced pressure. The residue was added on a column of silica gel, and the fractions eluted with CH2Cl2.AcOEt (5:1) were collected, followed by distilling off the solvent, thus yielding 321 mg (47%) of diphenylmethyl 7-(2-thienylacetamido)-2α-methyl-3-(1-methyl-1H-tetrazol-5-yl)thiomethylceph-3-em-4-carboxylate 1-oxide.

Workup

  1. washThe reaction solution was washed with 10% Na2S2O3 solution and with saturated aqueous NaCl solution
  2. dry with materialdried over MgSO4
  3. distillationto distill off the CH2Cl2 under reduced pressure
  4. additionThe residue was added on a column of silica gel
  5. washthe fractions eluted with CH2Cl2
  6. customAcOEt (5:1) were collected
  7. distillationby distilling off the solvent

Sources & evidence

ORD record
ord-70b8ef0e570d4bbb8030bd61ba8279d5
Source dataset
uspto-grants-1984_07
Patent number
US04463172

Reaction notes

Loading…