Methanol → 2-Hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetic acid

HRID 77119ノート

反応式

HRID 77119 の反応式
[OH:1][CH:2]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]=[C:17]([C:19]3[O:23][N:22]=[C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:20]=3[C:30]([F:33])([F:32])[F:31])[O:16][N:15]=2)=[CH:10][CH:9]=1)[C:3]([O:5]CC)=[O:4].CO.[Li+].[OH-]>C1COCC1>[OH:1][CH:2]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]=[C:17]([C:19]3[O:23][N:22]=[C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:20]=3[C:30]([F:31])([F:32])[F:33])[O:16][N:15]=2)=[CH:10][CH:9]=1)[C:3]([OH:5])=[O:4]

参加物

5

反応物 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 68232676(R/S)-Ethyl 2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetate

生成物 1

HCID 674589572-Hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetic acid収率 73.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(R/S)-Ethyl 2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetate (150 mg, 0.327 mmol) was dissolved in THF (2 mL) at 0° C. and MeOH (0.5 mL) and 1N LiOH (0.327 mL, 0.327 mmol) were added. After stirring for 1 h, the solution was concentrated and then EtOAc was added. The EtOAc was washed with 1 N HCl aqueous. The organic layer was dried (MgSO4), filtered and concentrated to give (R/S)-2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetic acid Int-V (110 mg, 0.240 mmol, 73.4% yield): LCMS=431.9[M+H]+, 1H NMR (400 MHz, methanol-d4) δ ppm 8.19 (2 H, d, J=8.79 Hz), 7.51-7.79 (7 H, m), 5.26 (1 H, s).

後処理

  1. concentrationthe solution was concentrated
  2. additionEtOAc was added
  3. washThe EtOAc was washed with 1 N HCl aqueous
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-46498fbb1b3e47d8bb00f11eb1320e77
出典データセット
uspto-grants-2014_09
特許番号
US08835470B2

反応ノート

読み込み中…