Methyl formate → Nalpha-formyl-DL-methionine amide

HRID 1602756Notes

Reaction equation

HRID 1602756 reaction equation
[NH2:1][CH:2]([C:7]([NH2:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].[CH:10](OC)=[O:11]>>[CH:10]([NH:1][CH:2]([C:7]([NH2:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6])=[O:11]

Participants

3

Reactant 2

HCID 7865Methyl formateHCID 5687422-Amino-4-(methylthio)butanamide

Product 1

HCID 18329562Nalpha-formyl-DL-methionine amideYield 55%

Procedure

30 g (0.20 mole) DL-methionine amide were agitated with 250 ml methyl formate for two days at room temperature, during which fine, slightly yellow crystals developed. They were filtered off and recrystallized out of a mixture of 150 ml hexane and 160 ml ethanol. After cooling off, filtering, washing and drying, 23 g (55%) Nα -formyl-DL-methionine amide were obtained in the form of colorless crystals with a melting point of 121-122° C.

Workup

  1. filtrationThey were filtered off
  2. customrecrystallized out of a mixture of 150 ml hexane and 160 ml ethanol
  3. temperatureAfter cooling off
  4. filtrationfiltering
  5. washwashing
  6. customdrying

Sources & evidence

ORD record
ord-2bfbf8db1e2b4e1da89df3c38f14a767
Source dataset
uspto-grants-1999_11
Patent number
US05985632

Reaction notes

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