Ethyl Acetate → HCID 86592746, compound

HRID 1861988Notes

Reaction equation

HRID 1861988 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][C:10](=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:17][S:18]([O:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([CH2:29]Br)[CH:23]=1)(=[O:20])=[O:19].CCOC(C)=O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:29][C:24]2[CH:23]=[C:22]([O:21][S:18]([CH3:17])(=[O:20])=[O:19])[CH:27]=[CH:26][C:25]=2[Cl:28])[C:10](=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 18621194Phenol, 3-(bromomethyl)-4-chloro-, 1-methanesulfonate

Product 1

HCID 86592746HCID 86592746, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of piperazin-3-one-1-carboxylic acid tert-butyl ester (7.10 g, 35.3 mmol) in dry DMF (200 mL) at 0° C. was added sodium hydride (60% dispersion in mineral oil, 2.10 g, 53.0 mmol). The reaction mixture was stirred for 15 min, and then a solution of the benzylbromide from Step B (10.0 g, 35.3 mmol) in DMF (50 mL) was added dropwise. The reaction mixture was allowed to warm to room temperature overnight. The reaction was poured into EtOAc (300 ml), and washed with H2O (3×50 ml). The organic layer was dried with magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by column chromatography (60% ethyl acetate/hexane) to provide the title compound as a yellow oil.

Workup

  1. washwashed with H2O (3×50 ml)
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography (60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8f8ccf9ec9424b6cac89107b2c5e324c
Source dataset
uspto-grants-2003_03
Patent number
US06534506B2

Reaction notes

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