Ethyl chloroformate → Nalphaethoxycarbonyl-DL-methionine amide

HRID 2270883Notes

Reaction equation

HRID 2270883 reaction equation
[CH2:1]([O:3][C:4](Cl)=[O:5])[CH3:2].[NH2:7][CH:8]([C:13]([NH2:15])=[O:14])[CH2:9][CH2:10][S:11][CH3:12].[OH-].[Na+]>O>[CH2:1]([O:3][C:4]([NH:7][CH:8]([C:13]([NH2:15])=[O:14])[CH2:9][CH2:10][S:11][CH3:12])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 5687422-Amino-4-(methylthio)butanamide

Product 1

HCID 18329560Nalphaethoxycarbonyl-DL-methionine amideYield 57.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
2.5 °C

Procedure

106 ml (1.10 moles) ethylchloroformate were dripped into a solution of 150 g (1.02 moles) DL-methionine amide in 200 ml water at 5-10° C., during which the pH was maintained at 7-9 by adding sodium hydroxide solution. A thick, finely crystalline precipitate rapidly formed. A suspension which was just able to still be agitated was obtained by the addition of 800 ml water, which suspension was agitated 3 hours further at room temperature. Then the colorless crystals were filtered off, washed with water and recrystallized out of 900 ml water. After cooling to 0-5° C., filtering off, washing with water and drying, 129 g (57%) Nαethoxycarbonyl-DL-methionine amide with a melting point of 110-112° C. was obtained.

Workup

  1. temperaturewas maintained at 7-9
  2. customA thick, finely crystalline precipitate rapidly formed
  3. stirringwas agitated 3 hours further at room temperature
  4. filtrationThen the colorless crystals were filtered off
  5. washwashed with water
  6. customrecrystallized out of 900 ml water
  7. filtrationfiltering off
  8. washwashing with water
  9. customdrying

Sources & evidence

ORD record
ord-5caa714a8a65480ab992b12b1a4995b9
Source dataset
uspto-grants-2001_12
Patent number
US06333176B1

Reaction notes

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