Lithium hydroxide, monohydrate → HCID 10370074, compound

HRID 965643Notes

Reaction equation

HRID 965643 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][N:10]([CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][CH2:8][N:7]1[C:25](=[O:40])[CH2:26][CH:27]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:5])C.O[Li].O>C1COCC1.CO.O>[CH:12]([N:10]1[CH2:9][CH2:8][N:7]([C:25](=[O:40])[CH2:26][CH:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:6]([C:4]([OH:5])=[O:3])[CH2:11]1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 103247844-Benzhydryl-1-(3,3-diphenyl-propionyl)-piperazine-2-carboxylic acid ethyl ester

Product 1

HCID 10370074HCID 10370074, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of 4-Benzhydryl-1-(3,3-diphenyl-propionyl)-piperazine-2-carboxylic acid ethyl ester (0.51 g, 0.957 mmol), and LiOH.H2O (0.12 g, 2.87 mmol) in THF/MeOH/H2O (15:5:5) was stirred at room temperature for two days. The solvent was evaporated under reduced pressure, the residue was dissolved in water, acidified with 1N HCl to pH 3. The product was extracted with EtOAc, dried with MgSO4, and evaporated under reduced pressure. The product was purified by column chromatography (CH2Cl2:MeOH 15:1) to give the title compound in 95% yield.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. extractionThe product was extracted with EtOAc
  4. dry with materialdried with MgSO4
  5. customevaporated under reduced pressure
  6. customThe product was purified by column chromatography (CH2Cl2:MeOH 15:1)

Sources & evidence

ORD record
ord-c25aec51b3fa40519e670da4c9954493
Source dataset
uspto-grants-2005_10
Patent number
US06951862B2

Reaction notes

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