Sodium Methoxide → 8-(4-Fluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

HRID 706135ノート

反応式

HRID 706135 の反応式
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:6]=1[CH2:19][N:20]([CH2:31][C:32]([O:34][CH3:35])=[O:33])S(C1C=CC(C)=CC=1)(=O)=O)C.C[O-].[Na+]>CO>[CH3:35][O:34][C:32]([C:31]1[N:20]=[CH:19][C:6]2[C:5]([C:4]=1[OH:3])=[CH:10][CH:9]=[CH:8][C:7]=2[O:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)=[O:33]

参加物

4

反応物 2

HCID 10942334Sodium MethoxideHCID 671101063-(4-Fluoro-phenoxy)-2-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-benzoic acid ethyl ester

生成物 1

HCID 671104788-(4-Fluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester収率 93.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
0 °C

実験手順

To a stirred solution of 3-(4-fluoro-phenoxy)-2-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-benzoic acid ethyl ester (2.66 g, 5.17 mmol) in anhydrous methanol (8 mL) was added dropwise a solution of sodium methoxide (30% wt, 2.8 mL) and methanol (2 mL) at 0° C. The mixture was stirred at 0° C. for 10 minutes and then 3 h at room temperature before it was concentrated in vacuo. Water was added and the pH of the slurry was adjusted with 1 N HCl to pH=10. The resulting precipitate was collected by filtration, washed with water, saturated sodium bicarbonate, and water, and was dried in vacuo to give the title compound as a white solid (1.51 g): MS: (+) m/z 314.07 (M+1).

後処理

  1. customat 0° C
  2. concentration3 h at room temperature before it was concentrated in vacuo
  3. additionWater was added
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water, saturated sodium bicarbonate, and water
  6. customwas dried in vacuo

出典と根拠

ORDレコード
ord-1f9fff5cf9a94d52bf18801a19914c2b
出典データセット
uspto-grants-2015_11
特許番号
US09174976B2

反応ノート

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