반응 #411703

반응 방정식

benzyl alcohol

4-[[(tert-butoxycarbonyl)amino]methyl]cyclohexanecarboxylic acid

diphenylphosphoryl azide

triethylamine

→

benzyl-4-[[[tert-butoxycarbonyl]amino]methyl]cyclohexylcarbamate

용매

toluene

반응 조건

후처리

1. 1
   온도The mixture was slowly warmed
2. 2
   온도After cooling to 40° C.
3. 3
   온도the reaction mixture heated
4. 4
   온도at reflux for 20 h
5. 5
   기타The cold reaction mixture
6. 6
   세척was washed with water and brine
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   기타Removal of the solvent and recrystallization of the organic residue from ethyl acetate and diethyl ether

실험 절차

To a stirred suspension of 4-[[(tert-butoxycarbonyl)amino]methyl]cyclohexanecarboxylic acid (Maybridge Chemical Co., Ltd.) (45 g) and diphenylphosphoryl azide (44 ml) in toluene (600 ml) was added triethylamine (32 ml) over a period of 20 min whilst maintaining the internal temperature at −10-0° C. The mixture was slowly warmed and then stirred at 70° C. for 4 h. After cooling to 40° C., benzyl alcohol (36 ml) was added and the reaction mixture heated at reflux for 20 h. The cold reaction mixture was washed with water and brine and dried over anhydrous magnesium sulfate. Removal of the solvent and recrystallization of the organic residue from ethyl acetate and diethyl ether gave the title compound, benzyl-4-[[[tert-butoxycarbonyl]amino]methyl]cyclohexylcarbamate as a white solid, m.p. 129-131° C.

출처