4-Tert-butoxycarbonylmethyl-3-oxopiperazine-1-carboxylic acid benzyl ester → HCID 10584737, compound

HRID 1433035Notes

Reaction equation

HRID 1433035 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:13](=[O:25])[CH2:12]1)=O)C1C=CC=CC=1.[H][H]>CO.C(O)(=O)C.[Pd]>[C:21]([O:20][C:18](=[O:19])[CH2:17][N:14]1[CH2:15][CH2:16][NH:11][CH2:12][C:13]1=[O:25])([CH3:24])([CH3:22])[CH3:23]

Participants

6

Reactant 2

HCID 120515964-Tert-butoxycarbonylmethyl-3-oxopiperazine-1-carboxylic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 10584737HCID 10584737, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

4-tert-Butoxycarbonylmethyl-3-oxopiperazine-1-carboxylic acid benzyl ester (2.0 g, 5.75 mmol) is dissolved in 20 mL of methanol and 2 mL of acetic acid. Palladium (5%) on carbon (100 mg) is added, and the reaction mixture is stirred in an atmosphere of hydrogen overnight. The mixture is filtered and concentrated. Ethyl acetate is added, and the mixture is neutralized to pH 7 using 1N NaOH. The organic layer is concentrated to give (2-oxo-piperazin-1-yl)acetic acid tert-butyl ester (1.22 g).

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated
  3. additionEthyl acetate is added
  4. concentrationThe organic layer is concentrated

Sources & evidence

ORD record
ord-9dcb1646f8944f068a8a089bc2d38e89
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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