Ethyl chloroformate → HCID 21993433, compound

HRID 1977577Notes

Reaction equation

HRID 1977577 reaction equation
[CH:1]1([CH2:5][CH:6]([C:8]([OH:10])=[O:9])[NH2:7])[CH2:4][CH2:3][CH2:2]1.Cl[C:12]([O:14][CH2:15][CH3:16])=[O:13]>[OH-].[Na+]>[CH2:15]([O:14][C:12]([NH:7][CH:6]([C:8]([OH:10])=[O:9])[CH2:5][CH:1]1[CH2:4][CH2:3][CH2:2]1)=[O:13])[CH3:16]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 219880663-Cyclobutylalanine

Product 1

HCID 21993433HCID 21993433, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

10 g (70 mmol) of 3-cyclobutyl-DL-alanine [A. Burger et al., J. Med. Chem. 6, 221 (1963)] is dissolved, in 70 ml of 2M NaOH solution, cooled to +5° C. and 11.1 ml (116.2 mmol) of ethyl chloroformate is added in drops with constant stirring. Stirring is continued for 2 hours at this temperature, and for further 2 hours at room temperature. The reaction mixture is then washed with 20 ml of diethyl ether and after acidifying the solution to pH1 extracted with 3×20 ml of ethyl acetate. The pooled extracts are washed with brine, dried over anhydrous sodium sulphate and the solvent is evaporated at a pressure of 2.0-2.5 kPa. The resulted oil is considered to be the pure product [Yield: 13.1 g (87%), Rf(7)=0.8] and is used without further treatment in the next step.

Workup

  1. temperaturecooled to +5° C.
  2. waitfor further 2 hours at room temperature
  3. washThe reaction mixture is then washed with 20 ml of diethyl ether
  4. extractionextracted with 3×20 ml of ethyl acetate
  5. washThe pooled extracts are washed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. customthe solvent is evaporated at a pressure of 2.0-2.5 kPa

Sources & evidence

ORD record
ord-c9fb7ddcc91142d488af70006e30e9e7
Source dataset
uspto-grants-2001_05
Patent number
US06235707B1

Reaction notes

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