Methanol → 4-Oxo-4-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoic acid

HRID 1506521Notes

Reaction equation

HRID 1506521 reaction equation
[O:1]=[C:2]([C:9]1[CH:10]=[C:11]2[C:34](=[CH:35][CH:36]=1)[C:15]1=[N:16][O:17][C:18]([C:19]3[C:23]([C:24]([F:27])([F:26])[F:25])=[C:22]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[O:21][N:20]=3)=[C:14]1[CH2:13][CH2:12]2)[CH2:3][CH2:4][C:5]([O:7]C)=[O:6].C1COCC1.CO.[OH-].[Na+]>O>[O:1]=[C:2]([C:9]1[CH:10]=[C:11]2[C:34](=[CH:35][CH:36]=1)[C:15]1=[N:16][O:17][C:18]([C:19]3[C:23]([C:24]([F:27])([F:26])[F:25])=[C:22]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[O:21][N:20]=3)=[C:14]1[CH2:13][CH2:12]2)[CH2:3][CH2:4][C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 67171566Methyl 4-oxo-4-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate

Product 1

HCID 671704054-Oxo-4-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoic acidYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 4-oxo-4-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate (Preparation 109A, 22 mg, 0.044 mmol), THF (2 mL), MeOH (0.5 mL), water (0.5 mL) and 2N aqueous sodium hydroxide (0.2 mL, 0.400 mmol) was stirred at room temperature under nitrogen for 70 h. The reaction mixture was concentrated and the residue was acidified with 10% citric acid (1.5 mL) and extracted with dichloromethane (4×2 mL). The combined dichloromethane extracts were dried (sodium sulfate) and concentrated under reduced pressure to give 4-oxo-4-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoic acid (20 mg, 0.041 mmol, 94% yield) as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with dichloromethane (4×2 mL)
  3. dry with materialThe combined dichloromethane extracts were dried (sodium sulfate)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-70f309278b42425cb83cde33f72d9575
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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