Water → {4-[1-(5-Chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylcarbamoyl]-phenyl}-acetic acid

HRID 1715856노트

반응식

HRID 1715856 반응식
C[O:2][C:3](=[O:36])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:35])[NH:12][C:13]2[CH:22]=[C:21]3[C:16]([CH2:17][CH2:18][CH2:19][N:20]3[S:23]([C:26]3[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=3[O:33][CH3:34])(=[O:25])=[O:24])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1.[Li+].[OH-].O>CO.O1CCCC1>[Cl:32][C:30]1[CH:29]=[CH:28][C:27]([O:33][CH3:34])=[C:26]([S:23]([N:20]2[C:21]3[C:16](=[CH:15][CH:14]=[C:13]([NH:12][C:11]([C:8]4[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:36])=[O:2])=[CH:6][CH:7]=4)=[O:35])[CH:22]=3)[CH2:17][CH2:18][CH2:19]2)(=[O:25])=[O:24])[CH:31]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 68434762{4-[1-(5-Chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylcarbamoyl]-phenyl}-acetic acid methyl ester

생성물 1

HCID 24961622{4-[1-(5-Chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylcarbamoyl]-phenyl}-acetic acid

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

실험 절차

{4-[1-(5-Chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylcarbamoyl]-phenyl}-acetic acid methyl ester (121.00 mg, 0.23 mmol) was dissolved in methanol/tetrahydrofuran 1:1 (1.40 mL) and treated at room temperature with a 1N solution of LiOH in water (0.70 mL, 0.70 mmol). The mixture was stirred at room temperature for 4 hours, then the organic solvents were evaporated and the residual aqueous phase acidified with HCl 1N (0.70 mL). The precipitated solid was filtered washing with ether, then purified by flash chromatography (dichloromethane/methanol gradient) to yield {4-[1-(5-chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylcarbamoyl]-phenyl}-acetic acid as an off-white solid, 69.00 mg (59%), MS (ISP): m/e=513.5 (M−H).

후처리

  1. customthe organic solvents were evaporated
  2. filtrationThe precipitated solid was filtered
  3. washwashing with ether
  4. custompurified by flash chromatography (dichloromethane/methanol gradient)

출처 및 근거

ORD 기록
ord-0dbaf10588a94acd83031bd1250615dc
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07799933B2

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