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

HRID 706135노트

반응식

HRID 706135 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1f9fff5cf9a94d52bf18801a19914c2b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174976B2

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