Reaction equation
[SH:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.ON1C2C=CC=CC=2N=N1.COS(C1C=CC(C)=CC=1)(=O)=O.C1(N=C=NCCN2CCOCC2)CCCCC1.Cl.[CH3:51][O:52][C:53](=[O:56])[CH2:54][NH2:55]>CN(C=O)C.C(N1CCOCC1)C.C(OCC)(=O)C.CCCCCCC>[CH3:51][O:52][C:53]([CH2:54][NH:55][C:8]([C:3]1[C:2]([SH:1])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:10])=[O:56]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
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).
Workup
- stirringAfter having been stirred for 12 hours
- customthe mixture was partitioned between a saturated aqueous solution of ammonium chloride and dichloromethane
- customthe organic phase was dried
- concentrationconcentrated by evaporation
- customthe residue was purified by chromatography on silica gel (eluent: ethyl acetate/heptane)
- customyield
Sources & evidence
- ORD record
- ord-878e2a359c054f568ea7025c36f50a11
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05620995
Linked notes
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