1,1,1-Trifluorobut-3-en-2-ol → 3-[N-Dodecyl-N-2-[4-(E)-[3-hydroxy-4,4,4-trifluorobut-1-en-1-yl]phenoxy]ethylamino]propanoic Acid, Ethyl Ester

HRID 1700896Notes

Reaction equation

HRID 1700896 reaction equation
C(N(C(C)[C:25]([O:27][CH2:28][CH3:29])=[O:26])CCOC1C=CC(I)=CC=1)CCCCCCCCCCC.FC(F)(F)C(O)C=C.[CH2:39]([N:51]([CH2:69][CH2:70]CC(OCC)=O)[CH2:52][CH2:53][O:54][C:55]1[CH:60]=[CH:59][C:58](/[CH:61]=[CH:62]/[CH:63]([OH:68])[C:64]([F:67])([F:66])[F:65])=[CH:57][CH:56]=1)[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]>>[CH2:39]([N:51]([CH2:69][CH2:70][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:52][CH2:53][O:54][C:55]1[CH:60]=[CH:59][C:58](/[CH:61]=[CH:62]/[CH:63]([OH:68])[C:64]([F:66])([F:67])[F:65])=[CH:57][CH:56]=1)[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]

Participants

4

Reactant 3

HCID 132629561,1,1-Trifluorobut-3-en-2-olHCID 867571214-[N-dodecyl-N-2-[4-(E)-[3-hydroxy-4,4,4-trifluorobut-1-en-1-yl]phenoxy]ethylamino] butanoic acid, ethyl esterHCID 86757125[N-Dodecyl-N-[2-[4-iodophenoxy]ethyl]amino]propanoic acid, ethyl ester

Product 1

HCID 867571243-[N-Dodecyl-N-2-[4-(E)-[3-hydroxy-4,4,4-trifluorobut-1-en-1-yl]phenoxy]ethylamino]propanoic Acid, Ethyl EsterYield 76%

Procedure

[N-Dodecyl-N-[2-[4-iodophenoxy]ethyl]amino]propanoic acid, ethyl ester (0.95 g, 1.79 mmol) and 4,4,4-trifluorobut-1-en-3-ol (complex with 0.7 THF, 0.95 g, 5.4 mmol) were reacted by the general procedure as described in the preparation of 4-[N-dodecyl-N-2-[4-(E)-[3-hydroxy-4,4,4-trifluorobut-1-en-1-yl]phenoxy]ethylamino]butanoic acid, ethyl ester (Example 48) and afforded the title compound (0.633 g, 76%) as a colorless oil.

Sources & evidence

ORD record
ord-957a81e85b654ca895c9d95f5ba73eca
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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