Lithium Hydroxide → HCID 58524142, compound

HRID 536429Notes

Reaction equation

HRID 536429 reaction equation
[CH3:1][N:2]1[C:6]2[C:7]([C:28]([O:30]C)=[O:29])=[CH:8][CH:9]=[C:10]([C:11]3[CH2:15][C:14]([C:20]4[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=4)([C:16]([F:19])([F:18])[F:17])[O:13][N:12]=3)[C:5]=2[N:4]=[N:3]1.[OH-].[Li+]>O1CCCC1.O>[CH3:1][N:2]1[C:6]2[C:7]([C:28]([OH:30])=[O:29])=[CH:8][CH:9]=[C:10]([C:11]3[CH2:15][C:14]([C:20]4[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=4)([C:16]([F:19])([F:17])[F:18])[O:13][N:12]=3)[C:5]=2[N:4]=[N:3]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58524127HCID 58524127, compound

Product 1

HCID 58524142HCID 58524142, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-methyl-4-methoxycarbonyl-7-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzotriazole (0.1 g), lithiumhydroxide (11 mg) in tetrahydrofuran (10 ml) and water (5 ml) was stirred for 30 minutes. Tetrahydrofuran was removed and extracted with ethyl acetate (3×5 ml). The combined organic layers were dried over sodium sulfate and concentrated to give 3-methyl-7-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzotriazole-4-carboxylic acid. 1H-NMR (400 MHz, DMSO): 7.80 (t, 1H), 7.73 (d, 1H), 7.69 (d, 1H), 7.62 (d, 1H), 4.74 (bd, 1H), 4.50 (s, 3H), 4.46 (bd, 1H). LC-MS: m/z=458.98 (M+H).

Workup

  1. customTetrahydrofuran was removed
  2. extractionextracted with ethyl acetate (3×5 ml)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8d414367a9df4bdeaedd2cdbba9409bf
Source dataset
uspto-grants-2014_10
Patent number
US08859592B2

Reaction notes

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