Benzyl chloroformate → Diethyl 2-(benzyloxycarbonylamino)malonate

HRID 2293113Notes

Reaction equation

HRID 2293113 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH:5]([NH2:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].C(=O)([O-])O.[K+].[CH2:18]([O:25][C:26](Cl)=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCOCC1.O>[CH2:9]([O:8][C:6](=[O:7])[CH:5]([NH:11][C:26]([O:25][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:27])[C:4]([O:3][CH2:1][CH3:2])=[O:12])[CH3:10]

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 81272Propanedioic acid, 2-amino-, 1,3-diethyl esterHCID 516893Potassium Bicarbonate

Product 1

HCID 259787Diethyl 2-(benzyloxycarbonylamino)malonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-aminomalonic acid diethyl ester (10.0 g) in dioxane (60 ml) and water (36 ml), potassium hydrogen carbonate (10.4 g) was added. After completion of the effervescence benzylchloroformate (7.4 ml) was added. The mixture was stirred at 23° for 1.5 h then it was concentrated under reduced pressure, taken up with diethyl ether (400 ml) and washed with 5% HCl (50 ml) and brine (50 ml). The organic layer was dried over sodium sulphate and concentrated in vacuo to give the title compound as a colorless oil (13.6 g). T.l.c. EA/CH 1:4 Rf=0.25.

Workup

  1. concentrationit was concentrated under reduced pressure
  2. washwashed with 5% HCl (50 ml) and brine (50 ml)
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3495b0b06fae41468faa12523be56b97
Source dataset
uspto-grants-1997_11
Patent number
US05686449

Reaction notes

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