Lithium hydroxide, monohydrate → HCID 67169952, compound

HRID 1506460Notes

Reaction equation

HRID 1506460 reaction equation
[F:1][C:2]1[CH:29]=[C:28]2[C:5]([CH2:6][CH2:7][C:8]3[C:9]2=[N:10][O:11][C:12]=3[C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]=2[C:24]([F:27])([F:26])[F:25])=[CH:4][C:3]=1[C:30]([O:32]C)=[O:31].O.[OH-].[Li+]>C1COCC1.O>[F:1][C:2]1[CH:29]=[C:28]2[C:5]([CH2:6][CH2:7][C:8]3[C:9]2=[N:10][O:11][C:12]=3[C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:14]=2[C:24]([F:25])([F:27])[F:26])=[CH:4][C:3]=1[C:30]([OH:32])=[O:31]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrate2×HCID 67171662HCID 67171662, compound

Product 1

HCID 67169952HCID 67169952, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 8-fluoro-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carboxylate (Preparation 67C, 0.050 g, 0.109 mmol) and lithium hydroxide monohydrate (0.005 g, 0.119 mmol) in THF (4.0 mL) and water (4 mL) was stirred at room temperature for 4 h. An additional amount of lithium hydroxide monohydrate (0.005 g, 0.119 mmol) was added and the contents stirred at room temperature for 2 h. The reaction mixture was concentrated under vacuum and the residue was partitioned between ethyl acetate (3×10 mL) and water (5.0 mL). The ethyl acetate extracts were combined, dried, and concentrated to give 8-fluoro-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carboxylic acid as a white solid. [40 mg, 0.090 mmol, 83%]. The product had an HPLC ret. time=4.15 min. (condition B). LC/MS M+1=445.0.

Workup

  1. stirringthe contents stirred at room temperature for 2 h
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customthe residue was partitioned between ethyl acetate (3×10 mL) and water (5.0 mL)
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6010cbebe2b9493b8932159dd861b469
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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