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

HRID 1715856Notes

Reaction equation

HRID 1715856 reaction equation
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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

{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).

Workup

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

Sources & evidence

ORD record
ord-0dbaf10588a94acd83031bd1250615dc
Source dataset
uspto-grants-2010_09
Patent number
US07799933B2

Reaction notes

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