Trifluoroacetic acid → HCID 86703590, compound

HRID 1849715Notes

Reaction equation

HRID 1849715 reaction equation
[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[O:8][C:9]1[C:21]([CH:22]2[CH2:24][CH2:23]2)=[CH:20][C:12]([C:13]([O:15]C(C)(C)C)=[O:14])=[C:11]([F:25])[CH:10]=1.FC(F)(F)C(O)=O>ClCCl>[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[O:8][C:9]1[C:21]([CH:22]2[CH2:24][CH2:23]2)=[CH:20][C:12]([C:13]([OH:15])=[O:14])=[C:11]([F:25])[CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86703589HCID 86703589, compound

Product 1

HCID 86703590HCID 86703590, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-((1S,2S,4R)-bicyclo[2.2.1]heptan-2-yloxy)-5-cyclopropyl-2-fluorobenzoate (0.88 g, 2.54 mmol) in dichloromethane (40 mL) was added trifluoroacetic acid (1.9 mL, 25.4 mmol). The resulting mixture was stirred for 1 hour and then concentrated in vacuo. The residue was triturated with methanol to provide the title compound (0.24 g, 32%): 1H NMR (300 MHz, DMSO-d6) δ 12.77 (br s, 1H), 7.26 (d, J=8.5 Hz, 1H), 6.78 (d, J=13.2 Hz, 1H), 4.40-4.34 (m, 1H), 2.39-2.34 (m, 1H), 2.29-2.23 (m, 1H), 1.99-1.88 (m, 1H), 1.85-1.76 (m, 1H), 1.60-1.33 (m, 4H), 1.25-1.03 (m, 3H), 0.88-0.79 (m, 2H), 0.57-0.49 (m, 2H); MS (ES+) m/z 291.1 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated with methanol

Sources & evidence

ORD record
ord-5b4560dbbca7442aba2fd9a6a080475f
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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