Methyl chloroformate → Nalpha-methoxycarbonyl-DL-methionine amide

HRID 1602757ノート

反応式

HRID 1602757 の反応式
[CH3:1][O:2][C:3](Cl)=[O:4].[NH2:6][CH:7]([C:12]([NH2:14])=[O:13])[CH2:8][CH2:9][S:10][CH3:11].[OH-].[Na+]>O>[CH3:1][O:2][C:3]([NH:6][CH:7]([C:12]([NH2:14])=[O:13])[CH2:8][CH2:9][S:10][CH3:11])=[O:4]

参加物

5

反応物 3

HCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 5687422-Amino-4-(methylthio)butanamide

生成物 1

HCID 18329561Nalpha-methoxycarbonyl-DL-methionine amide収率 60.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

85 ml (1.11 moles) methylchloroformate 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 8-10 by the addition of sodium hydroxide solution. After 30 min of subsequent reaction 60 ml water were added, whereupon crystals formed which were filtered off, washed with water and dissolved in 250 ml water. This solution was extracted twice and the crystallization mother liquor extracted once with 500 ml methylene chloride in each instance. After rotating in, 162 g yellowish, crystalline residue remained. It was dissolved in 200 ml hot ethanol. Then, 400 ml MTBE were added and after the appearance of the first colorless crystals another 200 ml MTBE. After cooling in an ice bath, filtering off, washing with 200 ml MTBE and drying, 127 g (60%) Nα -methoxycarbonyl-DL-methionine amide with a melting point of 93-94° C. were obtained.

後処理

  1. additionwere added, whereupon crystals
  2. customformed which
  3. filtrationwere filtered off
  4. washwashed with water
  5. dissolutiondissolved in 250 ml water
  6. extractionThis solution was extracted twice
  7. extractionthe crystallization mother liquor extracted once with 500 ml methylene chloride in each instance
  8. dissolutionIt was dissolved in 200 ml hot ethanol
  9. additionThen, 400 ml MTBE were added
  10. temperatureAfter cooling in an ice bath
  11. filtrationfiltering off
  12. washwashing with 200 ml MTBE
  13. customdrying

出典と根拠

ORDレコード
ord-c059108710ef430ea77a31957c2a3bfc
出典データセット
uspto-grants-1999_11
特許番号
US05985632

反応ノート

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