Sodium hydride → HCID 86639104, compound

HRID 1099210Notes

Reaction equation

HRID 1099210 reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][NH:8][C:7](=[O:11])[C:6]1=[O:12])[CH2:2][CH2:3][CH3:4].[H-].[Na+].Br[CH:16]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:17]([O:19][CH3:20])=[O:18]>CN(C=O)C>[CH2:1]([N:5]1[CH2:10][CH2:9][N:8]([CH:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]([O:19][CH3:20])=[O:18])[C:7](=[O:11])[C:6]1=[O:12])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 2006272,3-Piperazinedione, 1-butyl-

Product 1

HCID 86639104HCID 86639104, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-butylpiperazine-2,3-dione (1.6 g, 9.1 mmol) in DMF (12 ml) at 0° C. was added sodium hydride (0.25 g, 10.4 mmol). After stirring for 20 min, methyl α-bromophenylacetate (1.6 ml, 10.0 mmol) was added to the reaction. The reaction was warmed to rt and allowed to stir for 18 h. The reaction was quenched with water, diluted with EtOAc, washed with 3M LiCl, water, and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified via flash chromatography (silica) to yield methyl (4-butyl-2,3-dioxopiperazin-1-yl)(phenyl)acetate (86%).

Workup

  1. stirringto stir for 18 h
  2. customThe reaction was quenched with water
  3. additiondiluted with EtOAc
  4. washwashed with 3M LiCl, water, and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified via flash chromatography (silica)

Sources & evidence

ORD record
ord-93b589bb11464d24a9933001350d6b50
Source dataset
uspto-grants-2012_03
Patent number
US08143405B2

Reaction notes

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