반응 #2270239

반응 방정식

2-((1R)-1-{2-[(benzyloxy)amino]-2-oxoethyl}-4-cyclohexylbutyl)-5-methyl-1,3-oxazole-4-carboxylic acid

N-methylmorpholine

1-hydroxybenzotriazole hydrate

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydochloride

N,N-dimethylethylenediamine

→

title compound

수율 92.2%

2-((1R)-1-{2-[(Benzyloxy)amino]-2-oxoethyl}-4-cyclohexylbutyl)-N-[2-(dimethylamino)ethyl]-5-methyl-1,3-oxazole-4-carboxamide

수율 92.2%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   세척washed with water, saturated sodium hydrogen carbonate solution and brine
2. 2
   건조dried over anhydrous magnesium sulphate
3. 3
   여과filtered
4. 4
   기타the solvent removed under reduced pressure
5. 5
   기타The residue was purified by column chromatography on silica gel eluting with a system of 94:4:0.4 (dichloromethane:methanol:ammonia)

실험 절차

A solution 2-((1R)-1-{2-[(benzyloxy)amino]-2-oxoethyl}-4-cyclohexylbutyl)-5-methyl-1,3-oxazole-4-carboxylic acid (Preparation 72) (200 mg, 0.47 mmol), N-methylmorpholine (77 □1,0.70 mmol), 1-hydroxybenzotriazole hydrate (63 mg, 0.47 mmol)and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydochloride (134 mg, 0.70 mmol) in dichloromethane (10 ml) was treated with N,N-dimethylethylenediamine (56 □1,0.51 mmol) and stirred at room temperature for 18 hours. The reaction mixture was diluted with dichloromethane and washed with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulphate, filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a system of 94:4:0.4 (dichloromethane:methanol:ammonia) to afford the title compound as a white solid (216 mg).

출처