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

HRID 568892

反応式

HRID 568892 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 73974-Toluenesulfonyl chloride触媒HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b2d631c393184639b9838869c6e2b4a4
出典データセット
uspto-grants-1988_03
特許番号
US04730044

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