Reaction #82109

Reaction equation

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

Solvents

ethyl acetate heptane

N-ethylmorpholine

DMF

Conditions

Workup

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

Procedure

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).

Source