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

HRID 127713

반응식

HRID 127713 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 53944913N-(Ethoxycarbonothioyl)-L-aspartic acid수율 89%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
45 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-202369a7eef443ae976c9ed556f237df
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04256897

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