Sodium Hydroxide → (2R)-4-[(Benzyloxy)carbonyl]-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid

HRID 2271022Notes

Reaction equation

HRID 2271022 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@@H:13]([C:24]([O:26]CC)=[O:25])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])[C@@H:13]([C:24]([OH:26])=[O:25])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53776461HCID 53776461, compound

Product 1

HCID 7010654(2R)-4-[(Benzyloxy)carbonyl]-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acidYield 91.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl (2R)-4-benzyloxycarbonyl-1-tert-butoxycarbonyl-2-piperazinecarboxylate (15.0 g) in dioxane (100 ml) was added 1N NaOH (76.4 ml) at ambient temperature for 4 hours, the reaction mixture was concentrated in vacuo to remove dioxane. The resulting solution was acidified with 3N HCl to be pH2 and extracted with AcOEt (300 ml). The organic layer was washed with saturated NaCl solution, dried over MgSO4 and evaporated in vacuo to give 12.8 g of (2R)-4-benzyloxycarbonyl-1-tert-butoxycarbonyl-2-piperazinecarboxylic acid as an amorphous powder.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customto remove dioxane
  3. extractionextracted with AcOEt (300 ml)
  4. washThe organic layer was washed with saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-ac189ac5e14e4c639b4e555a51ab2ccc
Source dataset
uspto-grants-2001_12
Patent number
US06333324B1

Reaction notes

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