m-Chloroperbenzoic acid → HCID 178434780, 화합물

HRID 1596359노트

반응식

HRID 1596359 반응식
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N:18]=[C:17]([CH3:19])[C:16]2[CH:20]=[CH:21][CH:22]=[C:23]([CH3:24])[C:15]=2[NH:14][C:13]1=[O:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:34])C=1>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N+:18]([O-:34])=[C:17]([CH3:19])[C:16]2[CH:20]=[CH:21][CH:22]=[C:23]([CH3:24])[C:15]=2[NH:14][C:13]1=[O:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 135536776HCID 135536776, 화합물

생성물 1

HCID 178434780HCID 178434780, 화합물수율 76.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of (3RS)-3-benzyloxycarbonylamino-5,9-dimethyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one (3.22 g) in methylene chloride (50 ml) was added m-chloroperbenzoic acid (2.50 g, 1.5 eq. mol) portionwise under stirring at ice-bath cooling. The mixture was stirred for 3 days at ambient temperatures. From the reaction mixture methylene chloride was removed in vacuo and to the residue was added an aqueous solution of sodium bicarbonate and stirred for several minutes. The mixture was extracted with ethyl acetate twice and the combined extract was washed with aqueous sodium bicarbonate, water twice and brine. The organic layer was dried over magnesium sulfate and evaporated in vacuo to afford an amorphous mass, which was triturated in methanol and collected by filtration to give (3RS)-3-benzyloxycarbonylamino-5,9-dimethyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one-4-oxide (2.59 g) as a crystalline powder. From the mother liquid, the second crop (0.25 g) of the desired powder was prepared by crystallization in a mixture of methanol and diisopropyl ether (3:1).

후처리

  1. temperaturecooling
  2. stirringThe mixture was stirred for 3 days at ambient temperatures
  3. customFrom the reaction mixture methylene chloride was removed in vacuo and to the residue
  4. additionwas added an aqueous solution of sodium bicarbonate
  5. stirringstirred for several minutes
  6. extractionThe mixture was extracted with ethyl acetate twice
  7. extractionthe combined extract
  8. washwas washed with aqueous sodium bicarbonate, water twice
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. customevaporated in vacuo
  11. customto afford an amorphous mass, which
  12. customwas triturated in methanol
  13. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-74c7651539044cc583949ea5e194cf96
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06291452B1

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