Sodium Hydroxide → 3-(4-{6-[5-(4-Methoxyphenyl)-[1,3,4]oxadiazol-2-yl]-1H-indol-2-yl}-3,5-dimethylphenyl)-propionic acid

HRID 1360791ノート

反応式

HRID 1360791 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[CH:22]=[C:21]4[C:17]([CH:18]=[C:19]([C:23]5[C:28]([CH3:29])=[CH:27][C:26]([CH2:30][CH2:31][C:32]([O:34]C)=[O:33])=[CH:25][C:24]=5[CH3:36])[NH:20]4)=[CH:16][CH:15]=3)=[N:11][N:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>O.CO.C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[CH:22]=[C:21]4[C:17]([CH:18]=[C:19]([C:23]5[C:28]([CH3:29])=[CH:27][C:26]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:25][C:24]=5[CH3:36])[NH:20]4)=[CH:16][CH:15]=3)=[N:11][N:10]=2)=[CH:5][CH:4]=1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 66966783Methyl 3-(4-{6-[5-(4-methoxyphenyl)-[1,3,4]oxadiazol-2-yl]-1H-indol-2-yl}-3,5-dimethylphenyl)-propionate

生成物 1

HCID 577865833-(4-{6-[5-(4-Methoxyphenyl)-[1,3,4]oxadiazol-2-yl]-1H-indol-2-yl}-3,5-dimethylphenyl)-propionic acid

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 22242641Methanol--water (1/1)溶媒

反応条件

温度
50 °C

実験手順

A mixture of methyl 3-(4-{6-[5-(4-methoxyphenyl)-[1,3,4]oxadiazol-2-yl]-1H-indol-2-yl}-3,5-dimethylphenyl)-propionate (35 mg, 73 μmol) and 1N NaOH (174 μL, 174 μmol) in 5 mL of 2:1 water/methanol and 5 mL THF was heated at 50° C. for 4 h. The solvent was removed under reduced pressure and the residue was stirred with water, and neutralized with 174 μL of 1 N HCl. The precipitate was filtered, washed with water, and dried to the title compound. H1-NMR (DMSO-d6): δ ppm 12.17 (s, broad, 1H), 11.62 (s, 1H), 8.08 (m, 3H), 7.76 (m, 2H), 7.19 (d, J=8.8 Hz, 2H), 7.06 (s, 2H), 6.46 (s, 1H), 3.88 (s, 3H), 2.82 (t, J=7.4 Hz, 2H), 2.58 (t, J=7.6 Hz, 2H), 2.12 (s, 6H). MS: m/z 468.2 (M+1); Retention time=1.33 min (Method 10). High Res MS (M+H): theory 468.1923, measured 468.1918.

後処理

  1. customThe solvent was removed under reduced pressure
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. dry with materialdried to the title compound

出典と根拠

ORDレコード
ord-51f269d53e4342299c91ff6979ec4085
出典データセット
uspto-grants-2011_02
特許番号
US07879850B2

反応ノート

読み込み中…