Lithium Hydroxide → 3-(1-TERT-BUTOXYCARBONYLPIPERAZIN-4-YL)PROPIONIC ACID

HRID 397694Notes

Reaction equation

HRID 397694 reaction equation
[OH-].[Li+].C([O:5][C:6](=[O:22])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)C>C(O)C>[NH3:9].[C:18]([O:17][C:15]([N:12]1[CH2:11][CH2:10][N:9]([CH2:8][CH2:7][C:6]([OH:22])=[O:5])[CH2:14][CH2:13]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 23000690Tert-butyl 4-(3-ethoxy-3-oxopropyl)piperazine-1-carboxylate

Product 2

HCID 222AmmoniaYield 10%HCID 27356443-(1-TERT-BUTOXYCARBONYLPIPERAZIN-4-YL)PROPIONIC ACIDYield 132.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1N Aqueous lithium hydroxide (15.6 ml) was added to a solution of tert-butyl 4-(3-ethoxy-3-oxopropyl)-1-piperazinecarboxylate (2.23 g) [see Preparation 89] in ethanol (95 ml). The reaction mixture was stirred for 18 hrs at room temperature, after which time the solvent was removed under reduced pressure. The crude product was purified by column chromatography on reverse phase MCI gel eluting with 1:1, acetonitrile:water and further purified on Dowex 50W-X8-100 ion-exchange resin eluting with water and then 10% ammonia to afford 3-[4-(tert-butoxycarbonyl)piperazino]propanoic acid (1.33 g) as a white solid.

Workup

  1. customafter which time the solvent was removed under reduced pressure
  2. customThe crude product was purified by column chromatography on reverse phase MCI gel
  3. washeluting with 1:1, acetonitrile
  4. customwater and further purified on Dowex 50W-X8-100 ion-exchange resin
  5. washeluting with water

Sources & evidence

ORD record
ord-6d7d970f34cd4be3a29bda963457bfad
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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