Trifluoroacetic acid → HCID 86703564, compound

HRID 1849693Notes

Reaction equation

HRID 1849693 reaction equation
[CH:1]1([C:4]2[C:5]([O:18][CH2:19][C:20]3([CH3:30])[CH2:29][CH2:28][C:23]4([C:25]([F:27])([F:26])[CH2:24]4)[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.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([C:4]2[C:5]([O:18][CH2:19][C:20]3([CH3:30])[CH2:29][CH2:28][C:23]4([C:25]([F:27])([F:26])[CH2:24]4)[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

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86703563HCID 86703563, compound

Product 1

HCID 86703564HCID 86703564, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of tert-butyl 5-cyclopropyl-4-((1,1-difluoro-6- methylspiro[2.5]octan-6-yl)methoxy)-2-fluorobenzoate (0.426 g, 1.00 mmol) and anisole (0.155 mL, 1.50 mmol) in dichloromethane (4.5 mL) was added trifluoroacetic acid (1.06 mL, 13.5 mmol). The reaction mixture was stirred at 0° C. for 3 hours before being quenched with water (5 mL). The reaction was diluted with dichloromethane (20 mL) and washed with water (4×10 mL) until the last wash was neutral as monitored by pH paper. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to afford the title compound (0.353 g, 95%) as a white solid: MS (ES−) m/z 367.3 (M−1).

Workup

  1. custombefore being quenched with water (5 mL)
  2. additionThe reaction was diluted with dichloromethane (20 mL)
  3. washwashed with water (4×10 mL) until the
  4. washlast wash
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6827ea9cf48b4b339b886d7ce769f227
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

Loading…