Tert-butyl 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoate → 4-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid

HRID 1849773Notes

Reaction equation

HRID 1849773 reaction equation
[C:1]([C:3]1([CH2:13][O:14][C:15]2[C:27]([CH:28]3[CH2:30][CH2:29]3)=[CH:26][C:18]([C:19]([O:21]C(C)(C)C)=[O:20])=[C:17]([F:31])[CH:16]=2)[CH:10]2[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:12][CH:4]1[CH2:5]3)[CH2:9]2)#[N:2]>ClCCl>[C:1]([C:3]1([CH2:13][O:14][C:15]2[C:27]([CH:28]3[CH2:30][CH2:29]3)=[CH:26][C:18]([C:19]([OH:21])=[O:20])=[C:17]([F:31])[CH:16]=2)[CH:4]2[CH2:5][CH:6]3[CH2:7][CH:8]([CH2:9][CH:10]1[CH2:11]3)[CH2:12]2)#[N:2]

Participants

3

Reactant 1

HCID 86703654Tert-butyl 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoate

Product 1

HCID 867036554-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acidYield 101.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoate (0.38 g, 0.88 mmol) in dichloromethane (30 mL) trifluoroacetic acid (10 mL) was added. The solution was stirred at ambient temperature for 16 hours and concentrated in vacuo to give the title compound as a pale yellow solid (0.33 g, quant.): 1H NMR (300 MHz, DMSO-d6) δ 12.86 (br s, 1H), 7.31 (d, J=8.4 Hz, 1H), 7.09 (d, J=13.0 Hz, 1H), 4.45 (s, 2H), 2.16-1.78 (m, 11H), 1.70-1.60 (m, 4H), 0.90-0.84 (m, 2H), 0.60-0.55 (m, 2H); MS (ES−) m/z 468.2 (M−1).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40e50f2069f74dc98c8eb5a6ee126b6e
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

Loading…