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Water → (2R)-4-[3-(2-Fluoro-3-methoxyphenyl)isoxazol-5-yl]-2-methyl-2-(methylsulfonyl)butanoic acid

HRID 404217
Notes
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Reaction equation

HRID 404217 reaction equation
[OH-].[Na+].[F:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=1[C:12]1[CH:16]=[C:15]([CH2:17][CH2:18][C@@:19]([CH3:29])([S:25]([CH3:28])(=[O:27])=[O:26])[C:20]([O:22]CC)=[O:21])[O:14][N:13]=1.O>O1CCOCC1>[F:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=1[C:12]1[CH:16]=[C:15]([CH2:17][CH2:18][C@@:19]([CH3:29])([S:25]([CH3:28])(=[O:27])=[O:26])[C:20]([OH:22])=[O:21])[O:14][N:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86709149ethyl(2R)-4-[3-(2-fluoro-3-methoxyphenyl)isoxazol-5-yl]-2-methyl-2-(methylsulfonyl)butanoate

Product 1

HCID 70817723(2R)-4-[3-(2-Fluoro-3-methoxyphenyl)isoxazol-5-yl]-2-methyl-2-(methylsulfonyl)butanoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

Procedure

Sodium hydroxide (1.0 M aqueous solution, 4.7 mL, 4.7 mmol, 4.0 equiv) was added to solution of ethyl(2R)-4-[3-(2-fluoro-3-methoxyphenyl)isoxazol-5-yl]-2-methyl-2-(methylsulfonyl)butanoate (0.47 g, 1.2 mmol, 1.0 equiv) in 1,4-dioxane (10 mL), and the reaction was allowed to stir overnight (18 h) at room temperature. Water (5 mL) was added, and the mixture was extracted with diethyl ether (25 mL). The aqueous phase was acidified to pH=3 with 1.0 M hydrochloric acid and then extracted with ethyl acetate (2×50 mL). The combined ethyl acetate phases were dried over potassium carbonate, filtered and concentrated under reduced pressure to provide a light tan solid (0.42 g, 96%). MS (LCMS) m/z 372.1 (M+1). 1H NMR (400 MHz, METHONAL-d4) δ1.68 (s, 3H) 2.26-2.41 (m, 1H) 2.61-2.74 (m, 1H) 2.85-3.00 (m, 1H) 3.04-3.15 (m, 1H) 3.16 (s, 3H) 3.92 (s, 3H) 6.65 (d, J=3.12 Hz, 1H) 7.18-7.24 (m, 2H) 7.36-7.44 (m, 1H).

Workup

  1. extractionthe mixture was extracted with diethyl ether (25 mL)
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. dry with materialThe combined ethyl acetate phases were dried over potassium carbonate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a5d49d14b640479bbafdae62a029b453
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08748466B2

Reaction notes

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