2-(2-Morpholin-4-yl-2-oxoethyl)-5-phenyl-pentanoic acid ethyl ester → 2-(2-morpholin-4-yl-2-oxo-ethyl)-5-phenyl-pentanoic Acid
Reaction equation
C([O:3][C:4](=[O:24])[CH:5]([CH2:15][C:16]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:17])[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)C.CO.O>>[N:18]1([C:16](=[O:17])[CH2:15][CH:5]([CH2:6][CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:4]([OH:24])=[O:3])[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1Participants
Procedure
To a solution of 2-(2-morpholin-4-yl-2-oxo-ethyl)-5-phenyl-pentanoic acid ethyl ester (604 mg, 1.81 mmol) in a 2:1 mixture of MeOH—H2O (12 ml) LiOH.H2O (228 mg, 5.43 mmol) was added and stirred overnight at room temperature. Ethanol was removed under reduced pressure, residue diluted with water (40 ml) and washed with ether. The aqueous layer was acidified to pH1 with 1N HCl and extracted with diethyl ether (3×25 ml). The combined organic extracts were dried with MgSO4 and concentrated under reduced pressure to give 2-(2-morpholin-4-yl-2-oxo-ethyl)-5-phenyl-pentanoic acid as a white solid (492 mg); 1H NMR (CDCl3) 8.0–7.5 (1H), 7.4–7.1 (m, 5H), 3.8–3.4 (m, 8H), 3.0 (m, 1H), 2.8 (dd, J=16.4, 9.6 Hz, 1H), 2.65 (t, J=7.2 Hz, 2H), 2.40 (dd, J=16.4, 4.3 Hz, 1H), 1.9–1.5 (m, 4H). MS: 306 (MH+).
Workup
- additionwas added
- customEthanol was removed under reduced pressure, residue
- additiondiluted with water (40 ml)
- washwashed with ether
- extractionextracted with diethyl ether (3×25 ml)
- dry with materialThe combined organic extracts were dried with MgSO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-6af270b1e84f49d294e6459f03ce5d2a
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07064123B1
Reaction notes
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