2-Azido-2-methylpropanoic acid → 2-(4-{(S)-[(tert-butylsulfinyl)amino][5-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}-1H-1,2,3-triazol-1-yl)-2-methylpropanoic acid

To a solution of 0.50 g (1.5 mmol) 2-methyl-N-{(1R)-1-[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]prop-2-ynyl}propane-2-sulfinamide in 3.0 mL water and 3.0 mL t-butanol was added 1.8 mL (1.5 mmol) 2-azido-2-methylpropanoic acid, 0.15 mL (0.15 mmol) 1.0M aqueous sodium ascorbate solution, and 15 μL (0.02 mmol) 1.0M solution of aqueous copper (II) sulfate. After 24 h at room temperature, the reaction mixture was quenched with water, acidified with 1N HCl, extracted three times with ethyl acetate, and washed with brine. The organic layer was dried over NaSO4, filtered and concentrated in vacuo. Purification by flash chromatography (silica gel, linear gradient 0-20% MeOH:CH2Cl2) afforded 0.30 g (44%) 2-(4-{(S)-[(tert-butylsulfinyl)amino][5-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}-1H-1,2,3-triazol-1-yl)-2-methylpropanoic acid. ES-MS [M+1]+=464.2.

1. customthe reaction mixture was quenched with water
2. extractionextracted three times with ethyl acetate
3. washwashed with brine
4. dry with materialThe organic layer was dried over NaSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customPurification by flash chromatography (silica gel, linear gradient 0-20% MeOH:CH2Cl2)

ORD 기록

ord-a01cda74f5494766a53ecf3f65f35f0a

출처 데이터셋

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08987310B2