Citric Acid → Tert-Butyl 2-amino-3-[4-(trifluoromethoxy)phenyl]propanoate
Reaction equation
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]Participants
Procedure
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%).
Workup
- customThe reaction solution (mainly THF) was evaporated
- extractionextracted with methylene chloride
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- customThe solvent was evaporated
- customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate, 94:6, 3:7, and 1:9, V/V)
Sources & evidence
- ORD record
- ord-3eb821511f21487ca85c87963aef49ba
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08344029B2
Reaction notes
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