m-Chloroperbenzoic acid → 2,2,2-Trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate-1-oxide

HRID 1660593노트

반응식

HRID 1660593 반응식
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[S:14][C@@H:15]2[CH:28]([NH:29][C:30](=[O:38])[CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:27](=[O:39])[N:16]2[CH:17]([C:19]([O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[O:20])[CH:18]=1>ClCCl>[CH3:12][CH:13]1[CH:18]=[C:17]([C:19]([O:21][CH2:22][C:23]([Cl:24])([Cl:25])[Cl:26])=[O:20])[N:16]2[C:27](=[O:39])[CH:28]([NH:29][C:30](=[O:38])[CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C@H:15]2[S:14]1=[O:9]

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 131803442,2,2-Trichloroethyl 2-methyl-7-(2-phenylacetamido)-2-cephem-4-carboxylate

생성물 1

HCID 705266812,2,2-Trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate-1-oxide수율 58.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 3-chloroperbenzoic acid (0.40 g.) in dichloromethane (10 ml.) was dropwise added to a solution of 2,2,2-trichloroethyl 2-methyl-7-(2-phenylacetamido)-2-cephem-4-carboxylate (0.92 g.) in dichloromethane (10 ml.) and the mixture was stirred for 1 hour. After the reaction was completed, the reaction mixture was filtered and the filtrate was washed in turn with a sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution, dried over magnesium sulfate, after which the solvent was distilled off under reduced pressure. The residue was recrystallized from ethanol to give 2,2,2-trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate-1-oxide (0.56 g.), mp 173° to 175° C.

후처리

  1. filtrationthe reaction mixture was filtered
  2. washthe filtrate was washed in turn with a sodium bicarbonate aqueous solution
  3. dry with materiala saturated sodium chloride aqueous solution, dried over magnesium sulfate
  4. distillationafter which the solvent was distilled off under reduced pressure
  5. customThe residue was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-1250d59d41bf439b80ab0cb02521b5f5
출처 데이터셋
uspto-grants-1981_12
특허 번호
US04308380

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