반응 #82109

반응 방정식

1-hydroxy-1H-benzotriazole

N-cyclohexyl-N'-(2-morpholinoethyl)-carbodiimide methyl-p-toluenesulfonate

glycine methyl ester hydrochloride

3-mercaptopyridine-2-carboxylic acid

→

3-Mercaptopyridine-2-carboxylic acid N-((methoxycarbonyl)methyl)amide

용매

ethyl acetate heptane

N-ethylmorpholine

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGAfter having been stirred for 12 hours
2. 2
   기타the mixture was partitioned between a saturated aqueous solution of ammonium chloride and dichloromethane
3. 3
   기타the organic phase was dried
4. 4
   농축concentrated by evaporation
5. 5
   기타the residue was purified by chromatography on silica gel (eluent: ethyl acetate/heptane)
6. 6
   기타yield

실험 절차

1.69 g of 3-mercaptopyridine-2-carboxylic acid were dissolved in 20 ml of DMF and 7.5 ml of N-ethylmorpholine, 1.7 g of 1-hydroxy-1H-benzotriazole, 5 g of N-cyclohexyl-N'-(2-morpholinoethyl)-carbodiimide methyl-p-toluenesulfonate and 4.3 g of glycine methyl ester hydrochloride were added successively at room temperature and whilst stirring. After having been stirred for 12 hours, the mixture was partitioned between a saturated aqueous solution of ammonium chloride and dichloromethane and the organic phase was dried and concentrated by evaporation; the residue was purified by chromatography on silica gel (eluent: ethyl acetate/heptane); yield, 0.65 g of colourless crystals of m.p. 178°-179° C. (ethyl acetate/heptane).

출처