Trifluoroacetic acid → HCID 178461261, compound

HRID 1849678Notes

Reaction equation

HRID 1849678 reaction equation
[CH:1]1([C:4]2[C:5]([O:18][CH2:19][C@H:20]3[CH2:25][CH2:24][C@H:23]([CH3:26])[CH2:22][CH2:21]3)=[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@H:20]3[CH2:25][CH2:24][C@H:23]([CH3:26])[CH2:22][CH2:21]3)=[CH:6][C:7]([F:17])=[C:8]([CH:16]=2)[C:9]([OH:11])=[O:10])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178450652HCID 178450652, compound

Product 1

HCID 178461261HCID 178461261, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 5-cyclopropyl-2-fluoro-4-((trans-4-methyl-cyclohexyl)methoxy)benzoate (5.95 g, 16.41 mmol) in anhydrous dichloromethane (28 mL) was added trifluoroacetic acid (14 mL). The mixture was stirred for 1 hour at ambient temperature, and then concentrated in vacuo. The solid was triturated with methanol to give the title compound (2.42 g, 48%):): 1H NMR (300 MHz, CDCl3) δ 12.8 (br s, 1H), 7.30 (d, J=8.5 Hz, 1H), 6.88 (d, J=13.1 Hz, 1H), 3.89 (d, J=6.1 Hz, 2H), 2.05-1.96 (m, 1H), 1.85-1.68 (m, 5H), 1.39-1.25 (m, 1H), 1.17-0.86 (m, 9H), 0.61-0.56 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-7e58e62163b247a4b7532d901ac65281
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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