Tetrabutylammonium Fluoride → HCID 57504508, compound

Tetrabutylammonium fluoride (1M in THF) (2028 μl, 2.03 mmol) was added to (S)-2-(tert-butyldimethylsilyloxy)-3-((S)-1-methoxypropan-2-yloxy)-N-(5-methylpyridin-2-yl)propanamide (Intermediate Y4) (388 mg, 1.01 mmol) in THF (5 mL) at 20° C. The resulting solution was stirred at room temperature for 3 hours. The reaction mixture was concentrated, diluted with ethyl acetate (50 mL), and washed sequentially with water (25 mL) and saturated brine (10 mL). The organic layer was dried (MgSO4) and evaporated. The crude product was purified by flash silica chromatography, eluting with 0 to 10% s MeOH in DCM to afford the product (200 mg, 74%). 1H NMR (400 MHz, DMSO) δ 1.04 (d, 3H), 2.24 (s, 3H), 3.17-3.23 (m, 4H), 3.25-3.31 (m, 1H), 3.55-3.73 (m, 3H), 4.16-4.23 (m, 1H), 5.94 (d, 1H), 7.59-7.65 (m, 1H), 7.98 (d, 1H), 8.12-8.16 (m, 1H), 9.48 (s, 1H); m/z (ESI+) (M+H)+=269.31; HPLC tR=1.11 min.

1. concentrationThe reaction mixture was concentrated
2. additiondiluted with ethyl acetate (50 mL)
3. washwashed sequentially with water (25 mL) and saturated brine (10 mL)
4. dry with materialThe organic layer was dried (MgSO4)
5. customevaporated
6. customThe crude product was purified by flash silica chromatography
7. washeluting with 0 to 10%

ORD record

ord-ac0504ab474f470eaffa1019f19856b4

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143263B2