Methyl chloroformate → HCID 21993429, compound

HRID 1977581Notes

Reaction equation

HRID 1977581 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][CH3:15])=[O:13]>[OH-].[Na+].O>[CH3:15][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]

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 219880663-Cyclobutylalanine

Product 1

HCID 21993429HCID 21993429, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
0 °C

Procedure

4.3 g (30 mmol) of 3-cyclobutyl-DL-alanine [A. Burger et al., J. Med. Chem. 6, 221 (1963)] is dissolved in 15 ml of 2M NaOH solution, cooled to 0° C. and simultaneously 16.5 ml of 2M NaOH solution and 2.55 ml (33 mmol) of methyl chloroformate are added with vigorous stirring. Stirring is continued at this temperature for 30 minutes and at room temperature for 2 hours. The reaction mixture is diluted with 40 ml of water, extracted with 10 ml of diethyl ether, then acidified to pH3 with 3M HCl. The product is extracted with ethyl acetate (4×20 ml), the extracts are pooled, washed with 20 ml of water, dried over anhydrous sodium sulphate and evaporated at a pressure of 2.0-2.5 kPa. The oily residue [5.3 g (88%), Rf(7)=0.61] is used without further purification in the next step.

Workup

  1. extractionextracted with 10 ml of diethyl ether
  2. extractionThe product is extracted with ethyl acetate (4×20 ml)
  3. washwashed with 20 ml of water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated at a pressure of 2.0-2.5 kPa
  6. customThe oily residue [5.3 g (88%), Rf(7)=0.61] is used without further purification in the next step

Sources & evidence

ORD record
ord-0db29f9e9a3a46348dc3bda1d2484ac9
Source dataset
uspto-grants-2001_05
Patent number
US06235707B1

Reaction notes

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