Trifluoroacetic acid → 4-((1-Cyanocyclohexyl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid

HRID 1849829Notes

Reaction equation

HRID 1849829 reaction equation
[C:1]([C:3]1([CH2:9][O:10][C:11]2[C:23]([CH:24]3[CH2:26][CH2:25]3)=[CH:22][C:14]([C:15]([O:17]C(C)(C)C)=[O:16])=[C:13]([F:27])[CH:12]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([C:3]1([CH2:9][O:10][C:11]2[C:23]([CH:24]3[CH2:26][CH2:25]3)=[CH:22][C:14]([C:15]([OH:17])=[O:16])=[C:13]([F:27])[CH:12]=2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86703715Tert-butyl 4-((1-cyanocyclohexyl)methoxy)-5-cyclopropyl-2-fluorobenzoate

Product 1

HCID 867037174-((1-Cyanocyclohexyl)methoxy)-5-cyclopropyl-2-fluorobenzoic acidYield 75.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-((1-cyanocyclohexyl)methoxy)-5-cyclopropyl-2-fluorobenzoate (0.498 g, 1.33 mmol) in dichloromethane (15 mL) was added trifluoroacetic acid (5 mL). The solution was stirred at ambient temperature for 1 hour and the solvent was concentrated in vacuo to dryness. The residue was triturated with diethyl ether (10 mL) to afford the title compound as a colorless solid (0.32 g, 75%): 1H NMR (300 MHz, DMSO-d6) 12.88 (br s, 1H), 7.32 (d, J=8.4 Hz, 1H), 6.93 (d, J=12.8 Hz, 1H), 4.14 (s, 2H), 2.02-1.95 (m, 3H), 1.72-1.65 (m, 3H), 1.51-1.43 (m, 4H), 1.24-1.18 (m, 1H), 0.91-0.85 (m, 2H), 0.61-0.56 (m, 2H); MS (ES−) m/z 316.2 (M−1).

Workup

  1. concentrationthe solvent was concentrated in vacuo to dryness
  2. customThe residue was triturated with diethyl ether (10 mL)

Sources & evidence

ORD record
ord-5e4282d1f04f422f85727bbb648b4fcd
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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