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

HRID 568892

Reaction equation

HRID 568892 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 73974-Toluenesulfonyl chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b2d631c393184639b9838869c6e2b4a4
Source dataset
uspto-grants-1988_03
Patent number
US04730044

Linked notes

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