Benzyl chloroformate → Ethyl 3-(((benzyloxy)carbonyl)amino)-2,2-dimethylpropanoate

HRID 264952Notes

Reaction equation

HRID 264952 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12]([O:14][C:15](=[O:21])[C:16]([CH3:20])([CH3:19])[CH2:17][NH2:18])[CH3:13]>C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH2:12]([O:14][C:15](=[O:21])[C:16]([CH3:20])([CH3:19])[CH2:17][NH:18][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[CH3:13]

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 421529Ethyl 3-amino-2,2-dimethylpropanoate

Product 1

HCID 22364460Ethyl 3-(((benzyloxy)carbonyl)amino)-2,2-dimethylpropanoate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

31 ml of 90% chloroformic acid benzyl ester are slowly added, at 0°-5° C., to 29.04 g of 3-amino-2,2-dimethylpropionic acid ethyl ester in 500 ml of ethyl acetate and 250 ml of 1M sodium hydrogen carbonate solution. The reaction mixture is stirred for 2 hours at 0°-5° C. and extracted with ethyl acetate. The organic phases are washed with saturated sodium chloride solution and then concentrated. The evaporation residue is purified by FC (1 kg of silica gel; eluant: ethyl acetate/hexane=1:3). The title compound is obtained: Rf (ethyl acetate/hexane=1:3)=0.28.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phases are washed with saturated sodium chloride solution
  3. concentrationconcentrated
  4. customThe evaporation residue is purified by FC (1 kg of silica gel; eluant: ethyl acetate/hexane=1:3)

Sources & evidence

ORD record
ord-37bcdd1329554382ac4b7b0debfaebbf
Source dataset
uspto-grants-1997_07
Patent number
US05646143

Reaction notes

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