Triethylamine → HCID 57979827, compound

Temperature

2.5 °C

N-(tert-Butoxycarbonyl)-N,O-dimethyl-L-serine (1.5 g, 6.43 mmol) and triethylamine (0.99 ml, 7.07 mmol) in tetrahydrofuran (20 ml) were cooled to −15 to −17° C. Ethyl chloroformate (0.68 ml, 7.07 mmol) was added drop wise followed by concentrated ammonium hydroxide (12 ml). The mixture was stirred at 0 to 5° C. for 2 hours. Saturated ammonium chloride solution was added and the layers separated. The aqueous layer was re-extracted with ethyl acetate and the combined organics dried (MgSO4) and concentrated under reduced pressure. The residues were dissolved in dioxane (10 ml) and 4M hydrogen chloride in dioxane (10 ml) was added and the mixture stirred for 1 hour. The mixture was evaporated and the residue dissolved in methanol, absorbed onto an SCX column, washed with methanol and eluted with 7N ammonia in methanol. Appropriate fractions were combined and evaporated to give N2,O-dimethyl-L-serinamide (576 mg, 68%) as a white, crystalline solid; 1H NMR spectrum: (DMSO d6) 1.92 (brs, 1H); 2.21 (s, 3H); 2.98 (t, 1H); 3.21 (s, 3H); 3.37 (m, 2H); 7.07 (brs, 1H); 7.30 (brs, 1H).

1. customthe layers separated
2. extractionThe aqueous layer was re-extracted with ethyl acetate
3. dry with materialthe combined organics dried (MgSO4)
4. concentrationconcentrated under reduced pressure
5. dissolutionThe residues were dissolved in dioxane (10 ml)
6. addition4M hydrogen chloride in dioxane (10 ml) was added
7. stirringthe mixture stirred for 1 hour
8. customThe mixture was evaporated
9. dissolutionthe residue dissolved in methanol
10. customabsorbed onto an SCX column
11. washwashed with methanol
12. washeluted with 7N ammonia in methanol
13. customevaporated

ORD record

ord-e059a71cbc67488bb70cd5a012195a67

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07632840B2