Trifluoroacetic acid → HCID 58497947, compound

HRID 1505265Notes

Reaction equation

HRID 1505265 reaction equation
C([O:5][C:6]([C:8]1[C:17]2[C:12](=[C:13]([C:18]3[CH2:22][C:21]([C:27]4[CH:32]=[C:31]([Cl:33])[CH:30]=[C:29]([Cl:34])[CH:28]=4)([C:23]([F:26])([F:25])[F:24])[O:20][N:19]=3)[CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:34][C:29]1[CH:28]=[C:27]([C:21]2([C:23]([F:25])([F:24])[F:26])[O:20][N:19]=[C:18]([C:13]3[CH:14]=[CH:15][CH:16]=[C:17]4[C:12]=3[CH:11]=[CH:10][CH:9]=[C:8]4[C:6]([OH:7])=[O:5])[CH2:22]2)[CH:32]=[C:31]([Cl:33])[CH:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58498015HCID 58498015, compound

Product 1

HCID 58497947HCID 58497947, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalene-1-carboxylic acid tert-butyl ester (Example 9.5) (1.0 g) in dichloromethane (2 ml) was added trifluoroacetic acid (2 ml) and the reaction mixture was stirred at ambient temperature for 4 hours. The reaction mixture was concentrated to give a solid which was washed with cyclohexane to give 5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalene-1-carboxylic acid (0.76 g). 1H-NMR (DMSO, 400 MHz): 8.95 (m, 2H), 8.20 (d, 1H), 7.90 (d, 1H), 7.65-7.80 (m, 5H), 4.50 (q, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give a solid which
  3. washwas washed with cyclohexane

Sources & evidence

ORD record
ord-ab5fa6b249794604a74146e5c857d7f4
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

Loading…