Hydrochloric Acid → 3',5'-Dichloro-4'-(2-oxo-3-piperidin-1-yl-pyrrolidin-1-ylmethyl)-biphenyl-4-carboxylic acid

HRID 1670844Notes

Reaction equation

HRID 1670844 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([Cl:17])[C:14]([CH2:18][N:19]3[CH2:23][CH2:22][CH:21]([N:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[C:20]3=[O:30])=[C:13]([Cl:31])[CH:12]=2)=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+].Cl>CO.C(OCC)(=O)C>[Cl:31][C:13]1[CH:12]=[C:11]([C:8]2[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][CH:9]=2)[CH:16]=[C:15]([Cl:17])[C:14]=1[CH2:18][N:19]1[CH2:23][CH2:22][CH:21]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[C:20]1=[O:30]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 576580003',5'-Dichloro-4'-(2-oxo-3-piperidin-1-yl-pyrrolidin-1-ylmethyl)-biphenyl-4-carboxylic acid methyl ester

Product 1

HCID 248521053',5'-Dichloro-4'-(2-oxo-3-piperidin-1-yl-pyrrolidin-1-ylmethyl)-biphenyl-4-carboxylic acidYield 58%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Treat a solution of 3′,5′-Dichloro-4′-(2-oxo-3-piperidin-1-yl-pyrrolidin-1-ylmethyl)-biphenyl-4-carboxylic acid methyl ester (0.190 g, 0.41 mmol) in methanol (15 mL) with 5N NaOH (0.82 mL), heat to reflux, and cool and stir at room temperature for 16 hours. Remove the solvent in vacuo to give a residue and neutralize with 1N HCl. Dilute the mixture with ethyl acetate and wash with water. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, purify with a 0 to 10% methanol in CH2Cl2 gradient to afford 0.106 g (58%) of the titled product. Rf=0.50 (4/1 CH2Cl2/methanol). ES MS (m/z): 447 (M+).

Workup

  1. temperatureheat
  2. temperatureto reflux
  3. temperaturecool
  4. customRemove the solvent in vacuo
  5. customto give a residue
  6. washwash with water
  7. dry with materialDry the organic layer (Na2SO4)
  8. customremove the solvent in vacuo
  9. customto afford crude product
  10. custompurify with a 0 to 10% methanol in CH2Cl2 gradient

Sources & evidence

ORD record
ord-d3d06c8420a541b9a3b1b5bcaf160ae0
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

Loading…