Tetrabutylammonium Fluoride → HCID 57504481, compound

A solution of tetrabutylammonium fluoride (1M in THF) (2.353 mL, 2.35 mmol) was added in one portion to a stirred solution of (S)-2-(tert-butyldimethylsilyloxy)-3-methoxy-N-(3-methyl-1,2,4-thiadiazol-5-yl)propanamide (Intermediate E2) (390 mg, 1.18 mmol) in tetrahydrofuran (10 mL). The resulting solution was stirred at ambient temperature for 4 hours. The reaction mixture was diluted with EtOAc (20 mL), and washed sequentially with water (10 mL) and saturated brine (10 mL). The organic layer was dried (MgSO4), filtered and evaporated. The residue was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane to afford (S)-2-hydroxy-3-methoxy-N-(3-methyl-1,2,4-thiadiazol-5-yl)propanamide (192 mg, 75%). 1H NMR (400 MHz, CDCl3) δ 2.49 (3H, s), 3.37 (3H, s), 3.60 (1H, d), 3.72 (2H, d), 4.46 (1H, q), 10.20 (1H, s); m/z (ESI+) (M+H)+=218.30; HPLC tR=0.89 min.

1. washwashed sequentially with water (10 mL) and saturated brine (10 mL)
2. dry with materialThe organic layer was dried (MgSO4)
3. filtrationfiltered
4. customevaporated
5. customThe residue was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane

ORD record

ord-28bb20c2f15540b4a52c31f73d018a12

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143263B2