Water → (S)-1,1-dibenzyl 2-ethyl propane-1,1,2-tricarboxylate

HRID 1487173노트

반응식

HRID 1487173 반응식
CS(O[C@@H:6]([CH3:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=O)=O.[C:13]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:25])[CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].[F-].[Cs+].O>CN(C=O)C>[CH:14]([C:13]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C@@H:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:12]

참가 물질

6

반응물 4

HCID 962WaterHCID 25953Cesium fluorideHCID 84754Dibenzyl malonateHCID 6364515ethyl (2S)-2-methylsulfonyloxypropanoate

생성물 1

HCID 86699671(S)-1,1-dibenzyl 2-ethyl propane-1,1,2-tricarboxylate수율 60%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

To a solution of (S)-ethyl 2-(methylsulfonyloxy)propanoate (28.4 g, 0.1 mol) in N,N′-dimethylformamide (400 mL) was added dibenzyl malonate (23.5 g, 0.12 mol) and cesium fluoride (15.2 g, 0.1 mol). The mixture was heated at 50° C. for 2 days. After cooled to room temperature, the mixture was poured into water and then extracted with ethyl acetate. The organic phases were combined, washed with brine, water and dried over anhydrous sodium sulfate, and then concentrated to afford the crude product (S)-1,1-dibenzyl 2-ethyl propane-1,1,2-tricarboxylate, which was purified by silica gel chromatography (23 g, yield 60%).

후처리

  1. temperatureAfter cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with brine, water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-110d67e3c77a4d46828757eda998cc6b
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428508B2

반응 노트

불러오는 중…