Sodium hydride → 4-Tert-butoxycarbonylmethyl-3-oxopiperazine-1-carboxylic acid benzyl ester

HRID 1433034Notes

Reaction equation

HRID 1433034 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13](=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 736777Benzyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 120515964-Tert-butoxycarbonylmethyl-3-oxopiperazine-1-carboxylic acid benzyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-oxopiperazine-1-carboxylic acid benzyl ester (4.68 g, 20 mmol) in 20 mL of DMF at) 0° C. is added sodium hydride (60%, 880 mg, 22 mmol). The suspension is stirred at ambient temperature for one t-butyl bromoacetate (4.68 g, 24 mmol) is added. The resulting mixture is stirred at ambient temperature overnight. After dilution with ethyl acetate (200 mL), the mixture is washed with brine (3×50 mL). The crude residue obtained from concentration of the organic phase is chromatographied on silica gel (30% ethyl acetate/Hexane) to give 5.57 g (80%) of 4-tert-butoxycarbonylmethyl-3-oxopiperazine-1-carboxylic acid benzyl ester as a white solid.

Workup

  1. additionis added
  2. washAfter dilution with ethyl acetate (200 mL), the mixture is washed with brine (3×50 mL)
  3. customThe crude residue obtained from concentration of the organic phase

Sources & evidence

ORD record
ord-dbd0927309104b65b685549502d1fd67
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

Loading…