Ethyl 2-amino-3-sulfanylpropanoate → Ethyl 2-Amino-3-(2-furanylthio)propanoate

HRID 568892

반응식

HRID 568892 반응식
CO[CH:3]1[CH:7]=[CH:6][CH:5](OC)[O:4]1.[NH2:10][CH:11]([CH2:17][SH:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(#N)C.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>[NH2:10][CH:11]([CH2:17][S:18][C:5]1[O:4][CH:3]=[CH:7][CH:6]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]

참가 물질

5

반응물 2

HCID 3297Ethyl 2-amino-3-sulfanylpropanoateHCID 789742,5-Dihydro-2,5-dimethoxyfuran

생성물 1

HCID 20149579Ethyl 2-Amino-3-(2-furanylthio)propanoate수율 31%

시약·촉매·용매 2

HCID 73974-Toluenesulfonyl chloride촉매HCID 6342Acetonitrile용매

실험 절차

To 16.25 g (125 mmol) of 2,5-dimethoxy-2,5-dihydrofuran and 23.20 g (125 mmol) of ethyl 2-amino-3-mercaptopropanoate in 100 ml dry acetonitrile was added approximately 0.15 g of tosyl chloride. The mixture was stirred 1 hour at room temperature under nitrogen during which time complete solution was attained which became very dark. The mixture was concentrated in vacuo, taken up in ethyl acetate, then extracted with aqueous NaHCO3 solution followed by saturated NaCl solution. The organic portion was dried over MgSO4, filtered then concentrated to 50 ml. The concentrate was then chromatographed to give 8.35 g (31.0%) of the title compound as a dark oil.

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with aqueous NaHCO3 solution
  3. dry with materialThe organic portion was dried over MgSO4
  4. filtrationfiltered
  5. concentrationthen concentrated to 50 ml
  6. customThe concentrate was then chromatographed

출처 및 근거

ORD 기록
ord-b2d631c393184639b9838869c6e2b4a4
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04730044

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