Trifluoroacetic acid → HCID 86703535, compound

HRID 1849669Notes

Reaction equation

HRID 1849669 reaction equation
[CH:1]1([C:4]2[C:5]([O:18][CH2:19][C:20]34[CH2:29][CH:24]5[CH2:25][CH:26]([CH2:28][CH:22]([C:23]5([F:31])[F:30])[CH2:21]3)[CH2:27]4)=[CH:6][C:7]([F:17])=[C:8]([CH:16]=2)[C:9]([O:11]C(C)(C)C)=[O:10])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([C:4]2[C:5]([O:18][CH2:19][C:20]34[CH2:29][CH:24]5[CH2:25][CH:26]([CH2:28][CH:22]([C:23]5([F:31])[F:30])[CH2:21]3)[CH2:27]4)=[CH:6][C:7]([F:17])=[C:8]([CH:16]=2)[C:9]([OH:11])=[O:10])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86703534HCID 86703534, compound

Product 1

HCID 86703535HCID 86703535, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 5-cyclopropyl-4-((4,4-difluoroadamantan-1-yl)-methoxy)-2-fluorobenzoate (1.0 g, 2.29 mmol) in dichloromethane (20 mL) was added trifluoroacetic acid (15 ml). The reaction mixture was stirred at ambient temperature for 2 hours and then concentrated in vacuo. The residue was triturated in mixture of dichloromethane and hexanes afforded the title compound as colorless solid (0.82 g, 94%): 1H NMR (300 MHz, DMSO-d6) δ 12.83 (s, 1H), 7.34 (d, J=8.5 Hz, 1H), 6.88 (d, J=13.1 Hz, 1H), 3.57 (s, 2H), 2.24 (br s, 2H), 2.04-1.95 (m, 2H), 1.87-1.68 (m, 10H), 0.93-0.87 (m, 2H), 0.65-0.56 (m, 2H); MS (ES+) m/z 381.1 (M+1); MS (ES−) m/z 379.2 (M−1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated in mixture of dichloromethane and hexanes

Sources & evidence

ORD record
ord-457dc89f9f564893a07f90b157c48ed8
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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