반응 #160361

반응 방정식

trans 4-methyl-cyclohexanecarboxylic acid

triphenylphosphine

3-(1,4-Dioxa-spiro[4.5]dec-8-ylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester

NaHCO3

N-chlorosuccinimide

→

3-[(1,4-Dioxa-spiro[4.5]dec-8-yl)-(trans 4-methyl-cyclohexanecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester

수율 66.3%

용매

ethyl acetate

1,2-dichloroethane

1,2-dichloroethane

반응 조건

후처리

1. 1
   workup.STIRRINGThe resulting mixture was then stirred for 18 h at 90° C.
2. 2
   온도cooled to room temperature
3. 3
   기타The aqueous phase was separated
4. 4
   세척washed with ethyl acetate (2×10 ml)
5. 5
   건조the combined organic layers were dried (Na2SO4)
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타The residue was purified by flash chromatography (0% to 30% EtOAc/Hexane)

실험 절차

To trans 4-methyl-cyclohexanecarboxylic acid (148 mg, 1.044 mmol) and triphenylphosphine (274 mg, 1.044 mmol) dissolved in 1,2-dichloroethane (1.5 ml) was added N-chlorosuccinimide (145 mg, 1.084 mmol). After 15 minutes of stirring at room temperature, a solution of 3-(1,4-Dioxa-spiro[4.5]dec-8-ylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester (300 mg, 0.803 mmol) in 1,2-dichloroethane (1.5 ml) was added. The resulting mixture was then 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) was added. 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 30% EtOAc/Hexane) to obtain 265 mg (66%) of 3-[(1,4-Dioxa-spiro[4.5]dec-8-yl)-(trans 4-methyl-cyclohexanecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester.

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