Ethyl Acetate → Dibenzyl 3(RS)-tert-butoxycarbonyl-2(R)-isobutylsuccinate

HRID 1857597노트

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HRID 1857597 반응식
[C:1]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:10])[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH3:19][C:20]([CH3:23])([O-])[CH3:21].[K+].[CH3:25][CH2:26][O:27][C:28]([CH3:30])=[O:29]>CN(C=O)C>[C:6]([O:5][C:3]([CH:2]([C:1]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10])[C@@H:30]([CH2:19][CH:20]([CH3:23])[CH3:21])[C:28]([O:27][CH2:26][C:25]1[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1)=[O:29])=[O:4])([CH3:9])([CH3:8])[CH3:7]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 2736712Benzyl tert-butyl malonateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 18660804Dibenzyl 3(RS)-tert-butoxycarbonyl-2(R)-isobutylsuccinate수율 89%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
0 °C

실험 절차

Benzyl tert-butyl malonate (24.9 g, 99.6 mmol) was dissolved in DMF (60 ml) and added portion wise with potassium tert-butoxide (13.4 g, 120 mmol) at 0° C. under stirring. The mixture was stirred at room temperature for 1 hour, then cooled to 0° C., and dropped in 1 hour with the solution of the Example 3-a compound (28.4 g, 99.6 mmol) dissolved in DMF (60 ml). After the reaction mixture was stirred at 5° C. overnight, it was added with AcOEt (2 l) and washed with a saturated aqueous solution of NaCl, 1N-HCl, a saturated aqueous solution of NaHCO3 and then the saturated aqueous solution of NaCl two times respectively. The organic layer was dried over anhydrous MgSO4, evaporated under reduced pressure and purified by column chromatography (silica gel; 750 g, elution with the mixed solvent; n-hexane: AcOEt=20:1), giving the title compound (40.0 g, 89%) of a colorless oil.

후처리

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. stirringAfter the reaction mixture was stirred at 5° C. overnight
  3. washwashed with a saturated aqueous solution of NaCl, 1N-HCl
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. customevaporated under reduced pressure
  6. custompurified by column chromatography (silica gel
  7. wash750 g, elution with the mixed solvent

출처 및 근거

ORD 기록
ord-14ca95b5eca140d4a62734f5567149e1
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06147114

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