Sodium Hydroxide → 2-[3',5'-Dichloro-4'-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-4-yloxy]-2-methyl-propionic acid

HRID 2235295Notes

Reaction equation

HRID 2235295 reaction equation
C([O:3][C:4](=[O:36])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[C:19]([Cl:21])[C:18]([CH2:22][CH:23]3[CH2:27][CH2:26][N:25]([CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)[C:24]3=[O:34])=[C:17]([Cl:35])[CH:16]=2)=[CH:11][CH:10]=1)([CH3:7])[CH3:6])C.[OH-].[Na+]>C(O)C>[Cl:35][C:17]1[CH:16]=[C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][C:5]([CH3:7])([CH3:6])[C:4]([OH:36])=[O:3])=[CH:10][CH:11]=2)[CH:20]=[C:19]([Cl:21])[C:18]=1[CH2:22][CH:23]1[CH2:27][CH2:26][N:25]([CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]2)[C:24]1=[O:34]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 116062232-[3',5'-Dichloro-4'-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-4-yloxy]-2-methyl-propionic acid ethyl ester

Product 1

HCID 116563312-[3',5'-Dichloro-4'-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-4-yloxy]-2-methyl-propionic acidYield 72.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 2-[3′,5′-Dichloro-4′-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-4-yloxy]-2-methyl-propionic acid ethyl ester (Example 195) (0.20 g, 0.37 mmol) in ethanol (10 mL) and treat with 5 N NaOH (0.4 mL). Heat the reaction to reflux for 1 hour, cool to room temperature and remove the solvent in vacuo. Aqueous 1 N HCl is added to adjust the pH to pH ˜1 and the mixture is extracted with ethyl acetate and water. The organic layer is dried (Na2SO4) to afford 136 mg (72%) of the title compound: LC-MS (ES+) m/z=exact mass calcd for C27H31Cl2NO4 503, found 504 and 506 (M+1 and M+3, 100%) and Rt (Purity at 214 nm)=6.03 min (96.7%).

Workup

  1. temperatureHeat
  2. customthe reaction
  3. temperatureto reflux for 1 hour
  4. customremove the solvent in vacuo
  5. additionAqueous 1 N HCl is added
  6. extractionthe mixture is extracted with ethyl acetate and water
  7. dry with materialThe organic layer is dried (Na2SO4)

Sources & evidence

ORD record
ord-8c8546785dc64a40b60d42962cfbec98
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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