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

HRID 404220Notes

Reaction equation

HRID 404220 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]1[O:14][N:13]=[C:12]([CH2:15][CH2:16][C@@:17]([CH3:27])([S:23]([CH3:26])(=[O:25])=[O:24])[C:18]([O:20]CC)=[O:19])[CH:11]=1.FC1C(OC)=CC=CC=1C1C=C(CC[C@@](C)(S(C)(=O)=O)C(O)=O)ON=1>>[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]1[O:14][N:13]=[C:12]([CH2:15][CH2:16][C@@:17]([CH3:27])([S:23]([CH3:26])(=[O:25])=[O:24])[C:18]([OH:20])=[O:19])[CH:11]=1

Participants

3

Reactant 2

HCID 70817723(2R)-4-[3-(2-Fluoro-3-methoxyphenyl)isoxazol-5-yl]-2-methyl-2-(methylsulfonyl)butanoic acidHCID 86709152ethyl(2R)-4-[5-(2-fluoro-3-methoxyphenyl)isoxazol-3-yl]-2-methyl-2-(methylsulfonyl)butanoate

Product 1

HCID 70817509(2R)-4-[5-(2-fluoro-3-methoxyphenyl)isoxazol-3-yl]-2-methyl-2-(methylsulfonyl)butanoic acidYield 99.1%

Procedure

The title compound (0.46 g, 95%) was prepared from ethyl(2R)-4-[5-(2-fluoro-3-methoxyphenyl)isoxazol-3-yl]-2-methyl-2-(methylsulfonyl)butanoate (0.50 g, 1.25 mmol) by following the procedure described for the synthesis of (2R)-4-[3-(2-fluoro-3-methoxyphenyl)isoxazol-5-yl]-2-methyl-2-(methylsulfonyl)butanoic acid (Example 1, Step B). MS (GCMS) m/z 372.1 (M+1). 1H NMR (400 MHz, METHONAL-d4) δ1.69 (s, 3H) 2.45-2.56 (m, 2H) 3.14 (d, J=9.95 Hz, 5H) 3.93 (s, 3H) 6.70-6.82 (m, 1H) 7.19-7.30 (m, 2H) 7.37-7.52 (m, 1H).

Sources & evidence

ORD record
ord-4c33e62cca9d4cd39b3d485eba2e254d
Source dataset
uspto-grants-2014_06
Patent number
US08748466B2

Reaction notes

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