Trifluoroacetic acid → HCID 11439992, compound

HRID 229266Notes

Reaction equation

HRID 229266 reaction equation
[C:1]1(=[C:8]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=2)[C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19]C(C)(C)C)=[O:18])=[C:11]([F:24])[CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]1(=[C:8]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=2)[C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])=[C:11]([F:24])[CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68977238HCID 68977238, compound

Product 1

HCID 11439992HCID 11439992, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The general hydrolysis procedure, described for 195 was followed. Thus, 1,1-dimethylethyl (2E)-3-{4-[cycloheptylidene(3-hydroxyphenyl)methyl]-2-fluorophenyl}-2-propenoate (198) (0.380 g, 0.9 mmol) in CH2Cl2 was treated with TFA to afford 0.305 g (92%) of the title compound as an off-white foam. 1H NMR (300 MHz, CD3OD): δ 7.76 (d, J=15.9 Hz, 1H), 7.59 (app t, J=7.8 Hz, 1H), 7.18 (app t, J=7.8 Hz, 1H), 7.04 (br d, J=8.1 Hz, 1H), 6.94 (br d, J=11.7 Hz, 1H), 6.67-6.60 (m, 3H), 6.56 (d, J=16.2 Hz, 1H), 2.34 (br s, 4H), 1.62 (br s, 8H). LCMS (ESI): m/z 365 (M−H)−. Anal. Calcd for C23H23FO3.1.5H2O, C, 70.38, H, 6.63, F, 4.84; Found: C, 69.96, H, 5.95, F, 4.73.

Workup

  1. customThe general hydrolysis procedure

Sources & evidence

ORD record
ord-0458ec78a7b64edeb2d15eb58d8eb5eb
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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