Hydrochloric Acid → (2S)-N,N-dimethyl-2-(methylamino)propanamide hydrochloride

To a solution of (S)-Boc-N-Me-Ala-OH (9.8 mmol, 2.00 g, from Bachem) in DMF (10 mL) were added 1-Hydroxy-1H-benzotriazole (10.8 mmol, 1.46 g) and EDCI (10.8 mmol, 2.08 g). The reaction mixture was stirred for 10 min before a 2M solution of dimethylamine in THF (11.8 mmol, 5.9 mL) was added. After stirring for 18 h at room temperature, water was added and the mixture was extracted several times with ethyl acetate. The combined organic layers were washed with 1N aqueous hydrochloric acid, aqueous sodium bicarbonate solution and water. After drying over magnesium sulfate, the volatiles were removed in vacuo. Yield: 1.86 g of a colorless oil (82%). The Boc-protected coupling product was dissolved in MeOH (19 mL) and treated with a 4N solution of HCl in dioxane (32.3 mmol, 8.1 mL). After stirring for 18 h at room temperature, the reaction mixture was evaporated to dryness to leave 1.41 g of a white solid (quantitative yield).

1. additionwas added
2. extractionthe mixture was extracted several times with ethyl acetate
3. washThe combined organic layers were washed with 1N aqueous hydrochloric acid, aqueous sodium bicarbonate solution and water
4. dry with materialAfter drying over magnesium sulfate
5. customthe volatiles were removed in vacuo
6. dissolutionThe Boc-protected coupling product was dissolved in MeOH (19 mL)
7. stirringAfter stirring for 18 h at room temperature
8. customthe reaction mixture was evaporated to dryness

ORD record

ord-bfa4305dafdf4c2fa57ce241788aa272

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580842B2