Dimethylamine, hydrochloride → HCID 28165235, compound

To a solution of Boc-L-alanine (2.32 g, 12.26 mmol) in DCM (20 mL) was added dimethylamine hydrochloride (2 g, 24.5 mmol) and DIPEA (3.1 g, 24.53 mmol). The solution was kept at 0° C. for 10 min, then HOBt (3.31 g, 24.5 mmol) and EDCI (4.6 g, 24.5 mmol) were added. The mixture was stirred at room temperature for 10 h, and then poured into water (40 mL) and extracted with DCM (100 mL×3). The extracts was washed with brine (50 mL), dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column (10-20% EtOAc in petroleum ether) to give Boc-L-alanine N,N-dimethyl amide as a colorless oil (1.1 g, 42%). 1H NMR (400 MHz, CDCl3) δ 8.48 (s, 1 H), 5.51 (brs, 1H), 4.56-4.63 (m, 1H), 3.03 (s, 3H), 2.93 (s, 3 H), 1.39 (s, 9H), 1.26 (d, J=6.8, 3 H).

1. extractionextracted with DCM (100 mL×3)
2. washThe extracts was washed with brine (50 mL)
3. dry with materialdried over anhydrous Na2SO4
4. filtrationfiltered
5. concentrationThe filtrate was concentrated under reduced pressure
6. customThe residue was purified by silica gel column (10-20% EtOAc in petroleum ether)

ORD record

ord-513f2202e97d4f27a3bcf301b12b368f

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309285B2