Lithium Hydroxide → 6-(Propane-2-sulfonylamino)-4'-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-2-carboxylic acid

HRID 746785Notes

Reaction equation

HRID 746785 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[S:25][CH:26]=[CH:27][C:28]=3[NH:29][S:30]([CH:33]([CH3:35])[CH3:34])(=[O:32])=[O:31])=[CH:20][CH:19]=2)=[C:7]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH:8]=[CH:9][CH:10]=1)=[O:4].[Li+].[OH-]>C1COCC1.CO.O.O>[CH3:17][CH:15]([S:12]([NH:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([C:3]([OH:4])=[O:2])[C:6]=1[C:18]1[CH:19]=[CH:20][C:21]([C:24]2[S:25][CH:26]=[CH:27][C:28]=2[NH:29][S:30]([CH:33]([CH3:34])[CH3:35])(=[O:31])=[O:32])=[CH:22][CH:23]=1)(=[O:13])=[O:14])[CH3:16]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 692513426-(Propane-2-sulfonylamino)-4'-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-2-carboxylic acid methyl ester

Product 1

HCID 692534356-(Propane-2-sulfonylamino)-4'-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Heat the mixture of 6-(propane-2-sulfonylamino)-4′-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-2-carboxylic acid methyl ester (46 mg, 0.08 mmol) and LiOH (30 mg, 1.25 mmol) in 3 ml of THF/Methanol/water (3/2/1, v/v/v) to 60 C for 3 h. Remove solvent and dissolve in water (35 mL). Wash with methylene chloride (2×20 mL). Neutralize the aq. solution to a pH between 2 and 3. Further purification with flash chromatography affords the title compound. MS (m/e): 521.1(M−1).

Workup

  1. temperatureHeat
  2. washWash with methylene chloride (2×20 mL)
  3. customFurther purification with flash chromatography

Sources & evidence

ORD record
ord-d1a92c9ff90140de8f92bd7e89cdb168
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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