4-[N-Dodecyl-N-2-[4-[3-hydroxy-4,4,4-trifluorobutyl]phenoxy]ethylamino]butanoic acid, ethyl ester → (2S, 4S)-1-N-Dodecyl-4-[4-[3-hydroxy-4,4,4-trifluoro-1-butyl]phenoxy]pyrrolidine2-carboxylic acid, methyl ester

HRID 1700903Notes

Reaction equation

HRID 1700903 reaction equation
[CH2:1]([N:13]1[CH2:17][C@@H:16]([O:18][C:19]2[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[CH:27]([OH:32])[C:28]([F:31])([F:30])[F:29])=[CH:21][CH:20]=2)[CH2:15][C@H:14]1[C:33]([O:35][CH3:36])=[O:34])[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][CH:27]([OH:32])[C:28]([F:29])([F:31])[F:30])=[CH:23][CH:24]=2)[CH2:15][C@H:14]1[C:33]([O:35][CH3:36])=[O:34])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

3

Reactant 2

HCID 867571234-[N-Dodecyl-N-2-[4-[3-hydroxy-4,4,4-trifluorobutyl]phenoxy]ethylamino]butanoic acid, ethyl esterHCID 86757131(2S, 4S)-1-N-Dodecyl-4-[4-(E)-[3-hydroxy-4,4,4-trifluorobut-1-en-1yl]phenoxy]pyrrolidine-2-carboxylic Acid, Methyl Ester

Product 1

HCID 86757130(2S, 4S)-1-N-Dodecyl-4-[4-[3-hydroxy-4,4,4-trifluoro-1-butyl]phenoxy]pyrrolidine2-carboxylic acid, methyl esterYield 99%

Procedure

(2S, 4S)-1-N-Dodecyl-4-[4-(E)-[3-hydroxy-4,4,4-trifluorobut-1-en-1yl]phenoxy]pyrrolidine-2-carboxylic Acid, Methyl Ester (552 mg., 1.07 mmol) was hydrogenated as described in the preparation of 4-[N-dodecyl-N-2-[4-[3-hydroxy-4,4,4-trifluorobutyl]phenoxy] ethylamino]-butanoic acid, ethyl ester and afforded the title compound (546 mg, 99%) as a clear oil. [a]D=−89.0° (c 0.4, CHCl3)

Sources & evidence

ORD record
ord-ff50492e58f24f36a368e5bd93112302
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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