Hydrochloric Acid → Diethyl 2-benzyloxycarbonylamino-2-(benzyloxycarbonylmethyl)malonate

HRID 57745

Reaction equation

HRID 57745 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28].Cl>CN(C=O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]([CH2:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 62576Benzyl bromoacetateHCID 259787Diethyl 2-(benzyloxycarbonylamino)malonate

Product 1

HCID 66725163Diethyl 2-benzyloxycarbonylamino-2-(benzyloxycarbonylmethyl)malonateYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of diethyl 2-benzyloxycarbonylaminomalonate (30 g) in anhydrous DMF (100 mL) was added portionwise with sodium hydride (60%, 4.27 g) with ice cooling and stirring, then the mixture was stirred at room temperature for 30 minutes, and then added with benzyl 2-bromoacetate (28.9 g), and the mixture was stirred overnight. The reaction mixture was poured into diluted hydrochloric acid, the mixture was extracted with ethyl acetate, and the extract was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography, and then purification was performed with n-hexane/ethyl acetate (4:1), to obtain the title compound (43.9 g, yield: 99%) as colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. stirringthe mixture was stirred overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washthe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. custompurification

Sources & evidence

ORD record
ord-602dde33759e487e961a51b22824aeaa
Source dataset
uspto-grants-2016_09
Patent number
US09434737B2

Linked notes

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