Hydrochloric Acid → (2S)-2-Ethoxy-3-[4-(2-{ethyl[4-(trifluoromethyl)benzyl]amino}-2-oxoethoxy)phenyl]propanoic Acid
Reaction equation
[CH2:1]([O:3][C@@H:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]([N:21]([CH2:33][CH3:34])[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)=[O:20])=[CH:13][CH:12]=1)[C:5]([O:7]CC)=[O:6])[CH3:2].Cl>C(#N)C.O.[Li+].[OH-]>[CH2:1]([O:3][C@@H:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]([N:21]([CH2:33][CH3:34])[CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:27][CH:28]=2)=[O:20])=[CH:13][CH:12]=1)[C:5]([OH:7])=[O:6])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of ethyl(2S)-2-ethoxy-3-[4-(2-{ethyl[4-(trifluoromethyl)benzyl]amino}-2-oxoethoxy)phenyl]propanoate ((0.308 g, 0.64 mmol) in acetonitrile (32 mL) was added aqueous 0.10 M LiOH (16 mL) and the solution was stirred at room temperature overnight. After neutralisation with 5% HCl, the solvent volume was reduced in vacuo and the remaining aqueous phase was diluted with water and aqueous 0.10 M LiOH (to a total volume of 100 mL, pH˜10) and washed with diethyl ether (2×100 mL). The aqueous phase was acidified with 5% HCl and extracted with ethyl acetate (3×100 mL). The combined organic phase was washed with 5% HCl (100 mL) and brine (100 mL), dried over Na2SO4, and concentrated in vacuo to afford 0.279 g (96%) of a colourless oil.
Workup
- washwashed with diethyl ether (2×100 mL)
- extractionextracted with ethyl acetate (3×100 mL)
- washThe combined organic phase was washed with 5% HCl (100 mL) and brine (100 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b531d58686694de6b77f52b73b14239e
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07462644B2
Reaction notes
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