4-[N-dodecyl-N-[2-[4-(3oxo-4,4,4-trifluorobut-1-yl)phenoxy]ethyl]amino]butanoic acid, ethyl ester → HCID 86757817, compound
Reaction equation
[CH2:1]([N:13]1[CH2:17][C@@H:16]([O:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH:27]([OH:32])[C:28]([F:31])([F:30])[F:29])=[CH:21][CH:20]=2)[CH2:15][C@@H:14]1[CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(N(CCCC(OCC)=O)CCOC1C=CC(CCC(=O)C(F)(F)F)=CC=1)CCCCCCCCCCC>>[CH2:1]([N:13]1[CH2:17][C@@H:16]([O:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][C:27](=[O:32])[C:28]([F:29])([F:31])[F:30])=[CH:23][CH:24]=2)[CH2:15][C@@H:14]1[CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]Participants
3
Procedure
(2S, 4S)-1-N-Dodecyl-4-[4-[3-hydroxy-4,4,4-trifluorobutyl]phenoxy]pyrrolidine-2-propanoic acid, methyl ester (150 mg, 0.276 mmol) was oxidized as described in the preparation of 4-[N-dodecyl-N-[2-[4-(3-oxo-4,4,4-trifluorobut-1-yl)phenoxy]ethyl]amino]butanoic acid, ethyl ester and afforded the title compound (70 mg, 47%) as a pale yellow oil. [a]D=−35.7° (c 0.84, CDCl3) Treatment of the above free amine with anhydrous hydrogen chloride (1.0 M in ether) gave the hydrochloride salt as a pale yellow foam.
Sources & evidence
- ORD record
- ord-d75e64ee97db4a60884c2f0a9e204aa2
- Source dataset
- uspto-grants-2002_02
- Patent number
- US06350892B1
Reaction notes
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