Methanol → N-(Ethoxycarbonothioyl)-L-aspartic acid

HRID 127713

反応式

HRID 127713 の反応式
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+].[O:12]([CH3:18])[C:13]([S:15]CC)=S.[CH3:19]O>O>[CH2:18]([O:12][C:13]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5])=[S:15])[CH3:19]

参加物

6

反応物 4

HCID 887MethanolHCID 5960L-Aspartic AcidHCID 14798Sodium HydroxideHCID 12515750Methyl ethyl xanthate

生成物 1

HCID 53944913N-(Ethoxycarbonothioyl)-L-aspartic acid収率 89%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
45 °C

実験手順

L-Aspartic acid (19.95 g, 0.150 mol) was suspended in 15 ml of water at 0° C., and 50% sodium hydroxide solution (24 g, 0.30 mol) was added dropwise with stirring. Methyl ethyl xanthate (22.44 g, 0.165 mol) in 15 ml of methanol was then added in one portion. The mixture was heated at 45° C. for 2 hours, cooled to room temperature, and washed with two portions of ethylene dichloride. The ethylene dichloride washes were discarded and the aqueous phase acidified with concentrated hydrochloric acid at 0° C. The solution was saturated with solid sodium chloride and extracted with two portions of ethyl acetate. The organic extracts were dried over anhydrous magnesium sulfate and evaporated in vacuo to afford 29.4 g (89%) of white crystalline N-ethoxythiocarbonyl-L-aspartic acid. mp 133° C.; nmr (DMSO-d6) δ1.23 (t, 3H, J=7 Hz), 2.67 (d, 2H, J=6 Hz), 4.37 (q, 2H, J=7 Hz), 4.93 (dt, 1H, J=6 Hz, 8 Hz), 9.26 (d, 1H, J=8 Hz).

後処理

  1. temperaturecooled to room temperature
  2. washwashed with two portions of ethylene dichloride
  3. customacidified with concentrated hydrochloric acid at 0° C
  4. extractionextracted with two portions of ethyl acetate
  5. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  6. customevaporated in vacuo

出典と根拠

ORDレコード
ord-202369a7eef443ae976c9ed556f237df
出典データセット
uspto-grants-1981_03
特許番号
US04256897

関連ノート

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