Tetrabutylammonium Fluoride → HCID 57504640, compound

Tetrabutylammonium fluoride (881 μl, 0.88 mmol) was added to (S)-2-(tert-butyldimethylsilyloxy)-3-((R)-2-methoxypropoxy)-N-(5-methylpyrazin-2-yl)propanamide (Intermediate Y11) (169 mg, 0.44 mmol) in THF (2203 μl) at room temperature under nitrogen. The resulting solution was stirred at room temperature for 3 hours. The reaction mixture was quenched with water (5 mL), extracted with ethyl acetate (3×10 mL), the organic layer was back washed with water (5 mL), dried (MgSO4) and evaporated. The crude product was purified by flash silica chromatography, eluting with 0 to 100% ethyl acetate in isohexane to afford the product (64.0 mg, 53.9%). 1H NMR (400 MHz, CDCl3) δ 1.13 (d, 3H), 2.53 (s, 3H), 3.33-3.43 (m, 5H), 3.68-3.82 (m, 2H), 4.04-4.11 (m, 1H), 4.33 (t, 1H), 4.53 (s, 1H), 8.12-8.15 (m, 1H), 9.19 (s, 1H), 9.43 (d, 1H); m/z (ESI+) (M+H)+=270.24; HPLC tR=1.04 min.

1. customThe reaction mixture was quenched with water (5 mL)
2. extractionextracted with ethyl acetate (3×10 mL)
3. washthe organic layer was back washed with water (5 mL)
4. dry with materialdried (MgSO4)
5. customevaporated
6. customThe crude product was purified by flash silica chromatography
7. washeluting with 0 to 100% ethyl acetate in isohexane

ORD record

ord-e8bf543ad25b40ebaf7a75ce3b2b4ea8

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143263B2