Tetrabutylammonium Fluoride → HCID 57504623, compound

A solution of tetrabutylammonium fluoride (1M in THF) (7.39 mL, 7.39 mmol) was added in one portion to a stirred solution of (S)-2-(tert-butyldimethylsilyloxy)-3-cyclobutoxy-N-(5-methylpyrazin-2-yl)propanamide (Intermediate R2) (2.7 g, 7.39 mmol) in tetrahydrofuran (25 mL) and the resulting solution was stirred at ambient temperature for 4 hours. The reaction mixture was concentrated under vacuum, diluted with ethyl acetate (50 mL) and washed sequentially with water (20 mL) and saturated brine (20 mL). The organic layer was dried (MgSO4) and evaporated. The residue was purified by flash silica chromatography, eluting with ethyl acetate to afford the product (1.5 g, 81%). 1H NMR (400 MHz, CDCl3) δ 1.48-1.56 (1H, m), 1.70-1.76 (1H, m), 1.90-2.00 (2H, m), 2.19-2.26 (2H, m), 2.54 (3H, s), 3.61 (1H, d), 3.67-3.73 (2H, m), 3.97-4.05 (1H, m), 4.35-4.38 (1H, m), 8.14 (1H, d), 9.15 (1H, s), 9.43 (1H, d); m/z (ESI+) (M+H)+=252; HPLC tR=1.31 min.

1. concentrationThe reaction mixture was concentrated under vacuum
2. additiondiluted with ethyl acetate (50 mL)
3. washwashed sequentially with water (20 mL) and saturated brine (20 mL)
4. dry with materialThe organic layer was dried (MgSO4)
5. customevaporated
6. customThe residue was purified by flash silica chromatography
7. washeluting with ethyl acetate

ORD record

ord-8cef96e3c5b64c77b09b6d8f5316f4e8

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143263B2