Lithium hydroxide, monohydrate → 2-(4-(Bis(4-chlorophenyl)methyl)-2-oxopiperazin-1-yl)acetic acid

HRID 494054Notes

Reaction equation

HRID 494054 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[N:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]([O:18]C)=[O:17])[C:11](=[O:20])[CH2:10]2)=[CH:4][CH:3]=1.O.[OH-].[Li+]>C1COCC1.CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)[N:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]([OH:18])=[O:17])[C:11](=[O:20])[CH2:10]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68928666Methyl 2-(4-(bis(4-chlorophenyl)methyl)-2-oxopiperazin-1-yl)acetate

Product 1

HCID 250636922-(4-(Bis(4-chlorophenyl)methyl)-2-oxopiperazin-1-yl)acetic acidYield 88%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of methyl 2-(4-(bis(4-chlorophenyl)methyl)-2-oxopiperazin-1-yl)acetate (160 mg, 393 μmol) in THF/MeOH/H2O=5:5:1 (5.5 mL) was added lithium hydroxide monohydrate (49.5 mg, 1.179 mmol) and the resulting solution was stirred overnight. The solvent was evaporated, diluted with water, adjusted to pH=5 with 10% HCl, extracted with DCM, dried over Na2SO4, filtered and evaporated to dryness under high vacuum. The residue was loaded onto flash column (SiO2, DCM to DCM/MeOH=100:5 to 100:10 to 100:15 to 100:20) to give 2-(4-(bis(4-chlorophenyl)methyl)-2-oxopiperazin-1-yl)acetic acid (136 mg) as a white solid.

Workup

  1. customThe solvent was evaporated
  2. additiondiluted with water
  3. extractionextracted with DCM
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness under high vacuum

Sources & evidence

ORD record
ord-550dd0282ebc41008fabb1055a46e285
Source dataset
uspto-grants-2009_05
Patent number
US07538114B2

Reaction notes

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