Lithium Hydroxide → (5-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-3-methyl-thiophene-2-sulfonylamine)-acetic acid

HRID 1819943Notes

Reaction equation

HRID 1819943 reaction equation
C[O:2][C:3](=[O:5])[CH3:4].[CH2:6]([C:8]([C:26]1[S:30][C:29]([S:31]([NH2:34])(=[O:33])=[O:32])=[C:28]([CH3:35])[CH:27]=1)([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]([OH:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[C:13]([CH3:25])[CH:12]=1)[CH2:9][CH3:10])[CH3:7].[Li+].[OH-]>O1CCOCC1>[C:3]([OH:5])(=[O:2])[CH3:4].[CH2:6]([C:8]([C:26]1[S:30][C:29]([S:31]([NH2:34])(=[O:33])=[O:32])=[C:28]([CH3:35])[CH:27]=1)([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]([OH:24])[C:20]([CH3:22])([CH3:23])[CH3:21])=[C:13]([CH3:25])[CH:12]=1)[CH2:9][CH3:10])[CH3:7]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68625699(5-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-3-methyl-thiophene-2-sulfonylamine)-acetic acid methyl ester

Product 1

HCID 68625349(5-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-3-methyl-thiophene-2-sulfonylamine)-acetic acidYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (5-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-3-methyl-thiophene-2-sulfonylamine)-acetic acid methyl ester (210 mg, 0.4 mmol) in dioxane (10 ml) is added 2N LiOH/H20 solution (10 ml) and stirred at RT overnight. The reaction is concentrated and partitioned between EtOAc/1N HCl. The organic layer is concentrated to give the title compound (180 mg, 88%).

Workup

  1. concentrationThe reaction is concentrated
  2. custompartitioned between EtOAc/1N HCl
  3. concentrationThe organic layer is concentrated

Sources & evidence

ORD record
ord-3f8e2d8949a946538c27a6e5ac097b5f
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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