Trifluoroacetic acid → 4-((Azepan-4-yloxy)methyl)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazole

HRID 1689824Notes

Reaction equation

HRID 1689824 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][CH:11]([O:15][CH2:16][C:17]2[C:18]([C:25]3[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:32])=[N:19][O:20][C:21]=2[CH:22]2[CH2:24][CH2:23]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH:22]1([C:21]2[O:20][N:19]=[C:18]([C:25]3[C:26]([Cl:32])=[CH:27][CH:28]=[CH:29][C:30]=3[Cl:31])[C:17]=2[CH2:16][O:15][CH:11]2[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]2)[CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 593693274-[5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-azepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 593693374-((Azepan-4-yloxy)methyl)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazoleYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 56 g (116.32 mmol) of 4-[5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-azepane-1-carboxylic acid tert-butyl ester in 150 mL of dichloromethane at 0° C. (ice bath) is treated with trifluoroacetic acid (150 mL, 1.98 mol). The mixture is stirred at room temperature under nitrogen for 2 hours. The reaction mixture is concentrated. The crude product is dissolved with EtOAc (300 mL), washed with a solution 2N—NaOH (2×100 mL) and washed with brine (1×100 mL). The organics are dried (Na2SO4), filtered and concentrated to afford 38 g of the desired compound as a yellow oil (86%). MS (m/e): 381 (M+1).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. dissolutionThe crude product is dissolved with EtOAc (300 mL)
  3. washwashed with a solution 2N—NaOH (2×100 mL)
  4. washwashed with brine (1×100 mL)
  5. dry with materialThe organics are dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f72af9b2aa5c416b82f2744ec34d39be
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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