反応 #160357

反応方程式

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

収率 49.0%

溶媒

1,2-dichloroethane

ethyl acetate

1,2-dichloroethane

反応条件

後処理

1. 1
   温度cooled to room temperature
2. 2
   その他The aqueous phase was separated
3. 3
   洗浄washed with ethyl acetate (2×10 ml)
4. 4
   乾燥the combined organic layers were dried (Na2SO4)
5. 5
   ろ過filtered
6. 6
   濃縮concentrated
7. 7
   その他The residue was purified by flash chromatography (0% to 20% EtOAc/Hexane)

実験手順

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.

出典