Hydrochloric Acid → 4-[4-Chloro-3-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-2-fluoro-phenyl]-butyric acid

HRID 2235245Notes

Reaction equation

HRID 2235245 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:31])[CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([CH2:17][CH:18]2[CH2:22][CH2:21][N:20]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[C:19]2=[O:29])[C:11]=1[F:30])C.Cl>CO>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][CH2:7][C:6]([OH:31])=[O:5])=[C:11]([F:30])[C:12]=1[CH2:17][CH:18]1[CH2:22][CH2:21][N:20]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[C:19]1=[O:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 592994384-[4-Chloro-3-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-2-fluoro-phenyl]-butyric acid ethyl ester

Product 1

HCID 592993614-[4-Chloro-3-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-2-fluoro-phenyl]-butyric acidYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Add 5 N NaOH solution (3 mL, 3 mmol) into 4-[4-chloro-3-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-2-fluoro-phenyl]-butyric acid ethyl ester (Preparation 79) (0.58 g, 1.4 mmol) in methanol (5 mL) at room temperature and stir for 30 minutes. Evaporate MeOH under reduced pressure and neutralize the residue by 1N HCl. Extract the mixture with ethyl acetate (10 mL) and separate the organic layer. Dry the organic layer with magnesium sulfate, filter and evaporate solvent under reduced pressure. Purify the residue by column chromatography to obtain the title product as white solid (300 mg, 55%): Mass spectrum (ion spray): m/z=396.0 (M+H).

Workup

  1. extractionExtract the mixture with ethyl acetate (10 mL)
  2. customseparate the organic layer
  3. dry with materialDry the organic layer with magnesium sulfate
  4. filtrationfilter
  5. customevaporate solvent under reduced pressure
  6. customPurify the residue by column chromatography

Sources & evidence

ORD record
ord-fdb962f2302f4826b3d6a3482604c098
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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