HCID 66849549, compound → HCID 178499353, compound

Participants

Reaction Steps

5-(3,3-Dimethyl-but-1-ynyl)3-(3-hydroxy-1-(S)-methyl-propylamino)-thiophene-2-carboxylic acid methyl ester (4.0 g, 12.94 mmol) was taken up in pyridine (100 mL). Trans-4-methyl-cyclohexanecarbonyl chloride (12.40 g, 77.66 mmol) was added and the reaction was placed in a 100° C. preheated oil bath and stirred for 16 h. After cooling to rt the solvent was removed under reduced pressure. The residue was partitioned between EtOAc and 2N HCl(aq), the organics dried over Na2SO4, and the solids filtered. Solvent was removed under reduced pressure and 5-(3,3-dimethyl-but-1-ynyl)-3-[(trans-4-methylcyclohexanecarbonyl)-[1-(S)-methyl-3-(trans-4-methyl-cyclohexanecarbonyloxy)-propyl]-amino]-thiophene-2-carboxylic acid methyl ester (4.15 g, 58%) was isolated by silica gel chromatography as a yellow solid.

Provenance & Evidence