Formic Acid → N-(2,4-dimethylphenyl)-4-(1-hydroxy-3-(2H-tetrazol-5-yl)propyl)-N-isobutylbenzenesulfonamide

Temperature

20 °C

N-(2,4-dimethylphenyl)-4-(1-hydroxy-3-(2-trityl-2H-tetrazol-5-yl)propyl)-N-isobutylbenzenesulfonamide (20 mg, 0.029 mmol), at room temperature was treated with a solution of HCl (6N in isopropanol, 2 mL, 12.00 mmol) and isopropanol (2 mL). The reaction mixture was stirred at 20° C. for 2 hours, then the solvent evaporated in vacuo and the crude partitioned between ethyl acetate (5 mL) and water (5 mL). The organic phase was separated by hydrophilic frit then evaporated in vacuo to give a residue. LCMS analysis showed the reaction was incomplete, so the residue was re-dissolved in dichloromethane (DCM) (2 mL) and treated with formic acid (0.5 mL, 13.04 mmol). The solution was left to stand for 2 hours. The solvent was evaporated in vacuo then dissolved in a 1:1 mixture of MeOH and DMSO and purified by MDAP (Method F) to give the required product, 3.69 mg. LCMS (M+1) 444, RT 1.09 mins.

1. customthe solvent evaporated in vacuo
2. customthe crude partitioned between ethyl acetate (5 mL) and water (5 mL)
3. customThe organic phase was separated by hydrophilic frit
4. customthen evaporated in vacuo
5. customto give a residue
6. waitThe solution was left
7. waitto stand for 2 hours
8. customThe solvent was evaporated in vacuo
9. dissolutionthen dissolved in a 1:1 mixture of MeOH and DMSO
10. custompurified by MDAP (Method F)

ORD record

ord-ec8d0d30fb54431c87ba1c4c748f9012

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150508B2