Hydrochloric Acid → HCID 66718168, compound

HRID 1514714Notes

Reaction equation

HRID 1514714 reaction equation
C[O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)=[N:14][O:15][C:16]=2[CH2:17][OH:18])=[N:6][CH:5]=1.O.[OH-].[Li+].Cl>C1COCC1.CO.C(OCC)(=O)C>[F:26][C:21]1[CH:20]=[C:19]([C:13]2[C:12]([CH2:11][O:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:27])=[O:2])=[CH:5][N:6]=3)=[C:16]([CH2:17][OH:18])[O:15][N:14]=2)[CH:24]=[CH:23][C:22]=1[F:25]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 667181646-[3-(3,4-Difluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

Product 1

HCID 66718168HCID 66718168, compoundYield 88.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-[3-(3,4-Difluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (1.00 g, 2.66 mmol) in THF (6.25 mL), methanol (1.75 mL), and water (6.25 mL) was treated with lithium hydroxide (130 mg, 5.31 mmol) overnight at room temperature. Addition of aqueous hydrochloride solution (1 N, 100 mL) and extraction with ethyl acetate afforded the title compound (850 mg, 88%) as a white solid. MS: m/e=361.1 [M−H]−.

Sources & evidence

ORD record
ord-e1f513bca64e46c18db0bf0c4e06d123
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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