Methanol → HCID 68730046, compound

HRID 2065756Notes

Reaction equation

HRID 2065756 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][N:10]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)(=[O:14])=[O:13])[CH2:9][CH2:8][N:7]1[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=1[CH3:29])=[O:5])C.[Li+].[OH-].CO.OS([O-])(=O)=O.[K+]>O1CCCC1>[Cl:21][C:17]1[CH:16]=[C:15]([S:12]([N:10]2[CH2:9][CH2:8][N:7]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=3[CH3:29])[CH:6]([C:4]([OH:5])=[O:3])[CH2:11]2)(=[O:13])=[O:14])[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 68729408HCID 68729408, compound

Product 1

HCID 68730046HCID 68730046, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3-chloro-benzenesulfonyl)-1-(4-fluoro-2-methyl-phenyl)-piperazine-2-carboxylic acid ethyl ester (730 mg) in tetrahydrofuran (20 mL) was added 1 M aqueous LiOH solution (16.6 mL) and methanol until a clear solution was obtained. The mixture was stirred at reflux for 1 h, 1M KHSO4 (20 mL) was added and the inorganic phase was extracted with ethyl acetate. The combined organic phases were dried (Na2SO4), filtered and evaporated to yield 4-(3-chloro-benzenesulfonyl)-1-(4-fluoro-2-methyl-phenyl)-piperazine-2-carboxylic acid as a light yellow solid, MS: 411.0 ([M−H, 1Cl]−).

Workup

  1. customwas obtained
  2. temperatureat reflux for 1 h
  3. extractionthe inorganic phase was extracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c8a4c90655744e40a30b4e5a68d2df4e
Source dataset
uspto-grants-2012_10
Patent number
US08288541B2

Reaction notes

Loading…