반응 #49825

반응 방정식

dimethylaminoethanol

Glycine methyl ester hydrochloride

3-(7-carboxy-1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazole-3-yl)-2-cyano-3-oxo-N-phenyl-propanamide

dicyclohexylcarbodiimide

→

N-[1,4-dihydro-1-phenyl-3-(2-phenylcarbamoyl-cyano-acetyl)indeno[1,2-c]pyrazol-7-yl] carbonyl-glycine methyl ester

수율 45.2%

용매

triethylamine

acetonitrile

반응 조건

후처리

1. 1
   workup.STIRRINGunder stirring at room temperature for 4 hours
2. 2
   여과The precipitate is filtered
3. 3
   세척washed with acetonitrile
4. 4
   농축The organic solution is concentrated in vacuo to a small volume
5. 5
   workup.ADDITIONdiluted with water
6. 6
   여과The obtained precipitate is filtered
7. 7
   세척washed with water
8. 8
   workup.DISSOLUTIONdissolved in chloroform
9. 9
   세척washed with 1N HCl
10. 10
    기타The organic solution is evaporated in vacuo to dryness
11. 11
    기타the residue is purified over a SiO2 column
12. 12
    기타Final crystallization from CH2Cl 2 /ethyl acetate

실험 절차

Glycine methyl ester hydrochloride (0.7 g) suspended in anhydrous acetonitrile (250 ml) is treated with triethylamine (0.56 g) under stirring at room temperature. To the suspension first 3-(7-carboxy-1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazole-3-yl)-2-cyano-3-oxo-N-phenyl-propanamide (2.3 g) and the dicyclohexylcarbodiimide (1.25 g) are added. The reaction mixture is kept under stirring at room temperature for 4 hours and then is basified to pH 8 by adding dimethylaminoethanol. The precipitate is filtered, washed with acetonitrile and then eliminated. The organic solution is concentrated in vacuo to a small volume, diluted with water, acidified to pH 2 with 1N HCl and then basified to pH 8 with 1N NaOH. The obtained precipitate is filtered, washed with water, dissolved in chloroform and washed with 1N HCl and then with water until neutral. The organic solution is evaporated in vacuo to dryness and the residue is purified over a SiO2 column using CHCl3 /methanol 90/10 as eluent. Final crystallization from CH2Cl 2 /ethyl acetate yields 1.2 g of pure N-[1,4-dihydro-1-phenyl-3-(2-phenylcarbamoyl-cyano-acetyl)indeno[1,2-c]pyrazol-7-yl] carbonyl-glycine methyl ester.

출처