Dimethylamine → (2S)-2-amino-N,N-dimethylbutanamide hydrochloride

Triethylamine (201.9 μL, 1.500 mmol) was added to a solution of (2S)-2-[(tert-butoxycarbonyl)amino]butanoic acid (101.6 mg, 0.500 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (221.1 mg, 0.500 mmol) in DCM (5 mL), followed by addition of 2.0 M of dimethylamine in tetrahydrofuran (0.500 mL). The mixture was stirred at RT for 4 h. The organic layer was separated. The aqueous layer was extracted with DCM (3×5 mL). The combined organic layers were washed with NaHCO3 (7.5%), and brine, dried over Na2SO4, filtered, and concentrated. The residue was treated with HCl in dioxane (4 M, 1.0 mL) at RT for 4 h. The volatiles were evaporated under reduced pressure. The residue was washed with ether and dried in-vacuo to give the desired product which was directly used in the next step without further purification. Analytical LCMS: (M+H)+=131.1.

1. customThe organic layer was separated
2. extractionThe aqueous layer was extracted with DCM (3×5 mL)
3. washThe combined organic layers were washed with NaHCO3 (7.5%), and brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. additionThe residue was treated with HCl in dioxane (4 M, 1.0 mL) at RT for 4 h
8. customThe volatiles were evaporated under reduced pressure
9. washThe residue was washed with ether
10. customdried in-vacuo

ORD record

ord-e7d8a9c4911349669ce9c0233f4ab50c

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143251B2