Citric Acid → Tert-Butyl 2-amino-3-[4-(trifluoromethoxy)phenyl]propanoate

HRID 1799294노트

반응식

HRID 1799294 반응식
C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C1(C(=[N:27][CH:28]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([O:43][C:44]([F:47])([F:46])[F:45])=[CH:39][CH:38]=2)[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[NH2:27][CH:28]([CH2:36][C:37]1[CH:38]=[CH:39][C:40]([O:43][C:44]([F:45])([F:46])[F:47])=[CH:41][CH:42]=1)[C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30]

참가 물질

4

반응물 2

HCID 311Citric AcidHCID 86636533Tert-butyl 2-[(diphenylmethylene)amino]-3-[4-(trifluoromethoxy)phenyl]propanoate

생성물 1

HCID 57972097Tert-Butyl 2-amino-3-[4-(trifluoromethoxy)phenyl]propanoate수율 95%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

According to the method described in the document (J. Am. Chem. Soc., (2003), 125, 5139-5151), a 1 M citric acid aqueous solution (52 mL) was added to a THF (52 mL) solution of tert-butyl 2-[(diphenylmethylene)amino]-3-[4-(trifluoromethoxy)phenyl]propanoate (2.44 g, 5.21 mmol) prepared in Reference Example 1 (1a). The mixture was stirred at room temperature for 4 hours. The reaction solution (mainly THF) was evaporated, neutralized with a sodium bicarbonate aqueous solution, and then extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated, and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate, 94:6, 3:7, and 1:9, V/V) to give 1.5 g of the title compound (colorless oil, yield: 95%).

후처리

  1. customThe reaction solution (mainly THF) was evaporated
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate, 94:6, 3:7, and 1:9, V/V)

출처 및 근거

ORD 기록
ord-3eb821511f21487ca85c87963aef49ba
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344029B2

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