反应详情

温度

60 °C

5-(3,3-Dimethyl-but-1-ynyl)-3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (0.10 g, 0.22 mmol) is dissolved in a 3:2:1 mixture of THF:methanol:H2O (5.0 mL) and treated with a 1N solution of LiOH.H2O (0.65 mL, 0.65 mmol). After 2 h of stirring at 60° C., the reaction mixture is concentrated under reduced pressure on a rotary evaporator. The mixture is partitioned between ethyl acetate and water. The water layer is acidified using 0.1 N HCl. The EtOAc layer is separated and dried over Na2SO4. Filtration and removal of the solvent under reduced pressure on a rotary evaporator followed by purification by column chromatography using methanol and dichloromethane (1:9) as eluent to obtain 5-(3,3-dimethyl-but-1-ynyl)-3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid as a solid, 30 mg (30%). ESI− (M−H): 444.3.

1. concentrationthe reaction mixture is concentrated under reduced pressure on a rotary evaporator
2. customThe mixture is partitioned between ethyl acetate and water
3. customThe EtOAc layer is separated
4. dry with materialdried over Na2SO4
5. filtrationFiltration and removal of the solvent under reduced pressure
6. customon a rotary evaporator
7. customfollowed by purification by column chromatography