HCID 67169668, compound → HCID 67171061, compound

HRID 1506558Notes

Reaction equation

[OH:1][C:2]([C:8]1[CH:9]=[C:10]2[C:33](=[CH:34][CH:35]=1)[C:14]1=[N:15][O:16][C:17]([C:18]3[C:22]([C:23]([F:26])([F:25])[F:24])=[C:21]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[O:20][N:19]=3)=[C:13]1[CH2:12][CH2:11]2)([CH3:7])[C:3]([O:5]C)=[O:4]>Cl.O1CCOCC1>[OH:1][C:2]([C:8]1[CH:9]=[C:10]2[C:33](=[CH:34][CH:35]=1)[C:14]1=[N:15][O:16][C:17]([C:18]3[C:22]([C:23]([F:24])([F:26])[F:25])=[C:21]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[O:20][N:19]=3)=[C:13]1[CH2:12][CH2:11]2)([CH3:7])[C:3]([OH:5])=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

Methyl 2-hydroxy-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)propanoate (Preparation 134C, isomer 1, 85 mg, 0.175 mmol) was dissolved in 4 N hydrochloric acid in dioxane (1 mL). The reaction mixture stirred at 60° C. for 48 h before it was concentrated to yield 2-hydroxy-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)propanoic acid (80 mg, 0.17 mmol, 97% yield): LC/MS M+1=472.03. Isomer 2: Methyl 2-hydroxy-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)propanoate (Preparation 134C, isomer 2, 83 mg, 0.171 mmol) was dissolved in 4 N hydrochloric acid in dioxane (1 mL). The reaction mixture was stirred at 60° C. for 48 h before it was concentrated to yield 2-hydroxy-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)propanoic acid (80 mg, 0.17 mmol, 99% yield): LC/MS M+1=472.03.

Workup

concentrationwas concentrated

Sources & evidence

ORD record: ord-00b3cfe97d204629a1759d559a771dd7
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216972B2

Reaction notes

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