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

HRID 851583노트

반응식

HRID 851583 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-5632cce1604a4fe18138cf7116c26994
출처 데이터셋
uspto-grants-1983_05
특허 번호
US04385176

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