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Sodium hydride → 2,3-dibenzyl 3-tert-butyl 1-cyclopropyl-2(R),3(R,S),3-propane-tricarboxylate

HRID 1108326
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HRID 1108326 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].[H-].[Na+].[CH:21]1([CH2:24][C@@H:25](OS(C(F)(F)F)(=O)=O)[C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[CH2:23][CH2:22]1>COCCOC.ClCCl>[CH:21]1([CH2:24][C@@H:25]([C:26]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:27])[CH:2]([C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[C:1]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:22][CH2:23]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 2736712Benzyl tert-butyl malonateHCID 22870963benzyl 3-cyclopropyl-2(R)-trifluoromethylsulphonyloxypropionate

생성물 1

HCID 1317218122,3-dibenzyl 3-tert-butyl 1-cyclopropyl-2(R),3(R,S),3-propane-tricarboxylate수율 95.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매
HCID 8071
1,2-Dimethoxyethane
용매

실험 절차

A solution of 3.8 g of benzyl tert-butyl malonate in 50 ml of 1,2-dimethoxyethane was treated with 0.504 g of an 80% dispersion of sodium hydride in mineral oil. The mixture was stirred at room temperature for 30 minutes and then cooled to 0°. A solution of 5.37 g of benzyl 3-cyclopropyl-2(R)-trifluoromethylsulphonyloxypropionate in 20 ml of dichloromethane was added dropwise at 0°. The mixture was stirred at 0° for 2 hours and then left to warm to room temperature overnight. The solvent was evaporated and the residue was dissolved in ethyl acetate. The solution was washed with water and saturated sodium chloride solution. After drying over anhydrous magnesium sulphate the solvent was evaporated to give 6.54 g of 2,3-dibenzyl 3-tert-butyl 1-cyclopropyl-2(R),3(R,S),3-propane-tricarboxylate as a 1:1 mixture of diastereoisomers in the form of an orange oil.

후처리

  1. temperaturecooled to 0°
  2. stirringThe mixture was stirred at 0° for 2 hours
  3. waitleft
  4. temperatureto warm to room temperature overnight
  5. customThe solvent was evaporated
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washThe solution was washed with water and saturated sodium chloride solution
  8. dry with materialAfter drying over anhydrous magnesium sulphate the solvent
  9. customwas evaporated

출처 및 근거

ORD 기록
ord-bb4cb048897f4ddbaf3716626d1af6c4
출처 데이터셋
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06066662

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