Bromochloromethane → (3S)-3-Benzyloxycarbonylamino-1-chloro-4-phenyl-2-butanone

HRID 413988노트

반응식

HRID 413988 반응식
[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14](=[O:23])OC1C1C=CC(OC)=CC=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:33][Cl:34].O1CCCC1.S([O-])(O)(=O)=O.[K+]>CCCCCC>[CH2:1]([O:8][C:9]([NH:11][C@@H:15]([CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:14](=[O:23])[CH2:33][Cl:34])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 6333BromochloromethaneHCID 8028TetrahydrofuranHCID 516920Potassium bisulfateHCID 11015253(4S)-N-benzyloxycarbonyl-2-(p-methoxyphenyl)-4-phenylmethyloxazolidin-5-one

생성물 1

HCID 99625(3S)-3-Benzyloxycarbonylamino-1-chloro-4-phenyl-2-butanone수율 62%

시약·촉매·용매 1

HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

(4S)-N-benzyloxycarbonyl-2-(p-methoxyphenyl)-4-phenylmethyloxazolidin-5-one (Tetrahedron Lett. 1995, 36, 42, 7761) (700 mg) and bromochloromethane (0.142 ml) were added to dehydrated tetrahydrofuran (16.8 ml), and they were cooled to −78° C. 1.54 Mn-butyllithium solution (1.42 ml) in hexane was added to the obtained mixture, and they were stirred for 33 minutes. 5% aqueous potassium hydrogensulfate solution was added to the reaction mixture to terminate the reaction. After the extraction with ethyl acetate at room temperature twice followed by drying over anhydrous magnesium sulfate, magnesium sulfate was removed. The obtained solution in ethyl acetate was analyzed by HPLC to find that (3S)-3-benzyloxycarbonylamino-1-chloro-4-phenyl-2-butanone (347 mg) was obtained in a yield of 62%.

후처리

  1. customto terminate
  2. customthe reaction
  3. extractionAfter the extraction with ethyl acetate at room temperature
  4. dry with materialby drying over anhydrous magnesium sulfate, magnesium sulfate
  5. customwas removed
  6. customwas obtained in a yield of 62%

출처 및 근거

ORD 기록
ord-d6730c6f6557447dbb53996b5e245712
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06570039B2

반응 노트

불러오는 중…