Triethylamine → HCID 45257257, compound

Temperature

0 °C

To a solution of the crude acid 2 (˜72.0 g, ˜0.810 mol, 1.0 equiv.) in CH2Cl2 (1600 mL) was added NEt3 (120 mL, 0.859 mol, 1.06 equiv.), DMAP (92 mg, 0.00082 mol, 0.001 equiv.) and O,N-Dimethyl-hydroxylamine hydrochloride (95.74 g, 0.982 mol, 1.21 equiv.) at 0° C. The resultant mixture was stirred for 10 minutes at −5° C. and EDCI (198.5 g, 1.035 mol, 1.27 equiv.) was added. The reaction mixture was stirred for 4 hours at 0° C. and diluted with hexanes (800 mL). The mixture was filtered through a pad of silica gel (2 cm thick of silica gel in a 3 L filtration funnel) and washed with Et2O (10×300 mL). The solvent was removed under reduced pressure to afford the crude amide 3 (92.2 g, 0.709 mmol, 87.5% for two steps) as slight-yellow oil. This crude product was dissolved in 1,2-dichloroethane (200 mL) and dried over molecular sieves at −20° C. for 2 hours before used in the next step).

1. filtrationThe mixture was filtered through a pad of silica gel (2 cm thick of silica gel
2. filtrationin a 3 L filtration funnel) and
3. washwashed with Et2O (10×300 mL)
4. customThe solvent was removed under reduced pressure

ORD record

ord-8420559ff8404eb5bd593f8ba818e391

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08410305B2