반응 #160357

반응 방정식

NaHCO3

2-Azido-4-methyl-cyclohexanecarboxylic acid chloride

4-Methyl-cyclohex-1-enecarboxylic acid chloride

3-Isopropylamino-5-phenyl-thiophene-2-carboxylic acid methyl ester

→

3-[(2-Azido-4-methyl-cyclohexanecarbonyl)-isopropyl-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester

수율 49.0%

용매

1,2-dichloroethane

ethyl acetate

1,2-dichloroethane

반응 조건

후처리

1. 1
   온도cooled to room temperature
2. 2
   기타The aqueous phase was separated
3. 3
   세척washed with ethyl acetate (2×10 ml)
4. 4
   건조the combined organic layers were dried (Na2SO4)
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The residue was purified by flash chromatography (0% to 20% EtOAc/Hexane)

실험 절차

To a solution of 3-Isopropylamino-5-phenyl-thiophene-2-carboxylic acid methyl ester (227 mg, 0.824 mmol) in 1,2-dichloroethane (2.5 ml) was added the 2:1 mixture of 2-Azido-4-methyl-cyclohexanecarboxylic acid chloride and 4-Methyl-cyclohex-1-enecarboxylic acid chloride (182 mg, 0.906 mmol) dissolved in 1,2-dichloroethane (0.5 ml). The resulting solution was stirred for 18 h at 90° C. and then cooled to room temperature. It was then diluted with ethyl acetate (10 ml) and a solution of saturated NaHCO3 (10 ml). The aqueous phase was separated and washed with ethyl acetate (2×10 ml) and the combined organic layers were dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (0% to 20% EtOAc/Hexane) to obtain 178 mg (49%) of 3-[(2-Azido-4-methyl-cyclohexanecarbonyl)-isopropyl-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester.

출처