Triethylamine → HCID 53686009, compound

To a round bottom flask charged with 4-((tert-butoxycarbonyl)amino)butanoic acid (0.5 g, 2.46 mmol) in DCM (10 mL) was added Et3N (1.03 mL, 7.36 mmol), EDCI (706 mg, 2.46 mmol), DMAP (30 mg, 0.246 mmol) and allowed to stir overnight at RT. The reaction was quenched with water (10 mL) and extracted with DCM (2×10 mL). Combined organics washed with 10% citric acid (10 mL), brine (10 mL), dried over Na2SO4 and concentrated in vacuo. The crude material was dissolved in AcOH (7 mL) and stirred at 65° C. for 1 h. The mixture was diluted with saturated bicarbonate (15 mL) and extracted with DCM (2×15 mL), and again worked up in the above manner. The title compound was obtained as a white solid (433 mg, 64%) and used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.57 (m, 2H), 7.20 (m, 2H), (4.98 (s, 2H), 3.24 (m, 2H), 2.95 (m, 2H), 1.92 (m, 2H), 1.47 (s, 9H). ESI-LRMS: [M+H]+=276 m/z.

1. customThe reaction was quenched with water (10 mL)
2. extractionextracted with DCM (2×10 mL)
3. washCombined organics washed with 10% citric acid (10 mL), brine (10 mL)
4. dry with materialdried over Na2SO4
5. concentrationconcentrated in vacuo
6. dissolutionThe crude material was dissolved in AcOH (7 mL)
7. stirringstirred at 65° C. for 1 h
8. additionThe mixture was diluted with saturated bicarbonate (15 mL)
9. extractionextracted with DCM (2×15 mL)

ORD record

ord-7a889c58856b4f0b90a8f6f3d474956f

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249087B2