反应详情

Prepared according to the procedure for the synthesis of {2-[3-cyclopentyl-3-(trans-4-methoxy-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid using 2-(trans-4-hydroxy-cyclohexyl)-isoindole-1,3-dione, 3-bromo-2-methylpropene cycloheptanone and 2-(2-amino-thiazol-5-ylsulfanyl)-2-methyl-acetic acid ethyl ester. The intermediate cyclohexyl-[trans-4-(2-methyl-allyloxy)-cyclohexyl]-amine was hydrogenated using the following procedure: Cyclo-hexyl-[4-(2-methyl-allyloxy)-cyclohexyl]-amine (540 mg, 2.15 mmol) was dissolved in 10 mL AcOH and the setup was flushed with N2 before 50 mg Pd/C was added. A balloon was charged with N2 and connected to the setup. The reaction mixture was stirred for three days at room temperature before the Pd was filtered off using a pad of celite. The filtrate was poured on 1 N NaOH (pH>12) and the mixture was extracted 3× with diethylether (50 mL), and dried (MgSO4) to give cyclohexyl-(trans-4-isobutoxy-cyclohexyl)-amine which was trans-formed to the title compound according to the procedure for the synthesis of {2-[3-cyclopentyl-3-(trans-4-methoxy-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid.

1. customPrepared
2. customthe setup was flushed with N2 before 50 mg Pd/C
3. additionwas added
4. additionA balloon was charged with N2
5. filtrationwas filtered off
6. additionThe filtrate was poured on 1 N NaOH (pH>12)
7. extractionthe mixture was extracted 3× with diethylether (50 mL)
8. dry with materialdried (MgSO4)