Sodium Carbonate → HCID 59656134, compound

Participants

Reaction Steps

A solution of 4-[3-(1-adamantyl)-5-mercapto-4H-1,2,4-triazol-4-yl]butan-1-ol (3-36) (60 mg) in conc. HCl (6 mL) was heated at 65° C. for 20 h. The cooled solution was added dropwise to 10% aqueous Na2CO3 (75 mL). The gum that precipitated was extracted four times with CH2Cl2. The combined extracts were dried (MgSO4) and evaporated in vacuo. The residue was purified by reverse phase HPLC on a C-18 silica gel column using an acetonitrile-0.1% trifluoroacetic acid gradient. Fractions containing the product were combined and rendered basic with excess 10% sodium carbonate. After removing most of the acetonitrile in vacuo, the basic solution was extracted five times with CH2Cl2. The combined extracts were dried (MgSO4) and evaporated in vacuo to give 3-(1-adamantyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[3,4-b][1,3]thiazepine (3-37).

Provenance & Evidence