L-Alanine → N-carbomethoxy-L-alanine

L-Alanine (2.0 g, 22.5 mmol) was dissolved in 10% aqueous sodium carbonate solution (50 mL), and a THF (50 mL) solution of methyl chloroformate (4.0 mL) was added to it. The reaction mixture was stirred under ambient conditions for 4.5 hours and concentrated in vacuo. The resulting white solid was dissolved in water and acidified with 1N HCl to a pH ˜2-3. The resulting solutions was extracted with ethyl acetate (3×100 mL), and the combined organic phase was dried (Na2SO4), filtered, and concentrated in vacuo to provide a colorless oil (2.58 g). 500 mg of this material was purified by a reverse phase HPLC (H2O/methanol/TFA) to provide 150 mg of Cap-12 as a colorless oil. 1H NMR (DMSO-d6, δ=2.5, 500 MHz) 7.44 (d, J=7.3, 0.8H), 7.10 (br s, 0.2H), 3.97 (m, 1H), 3.53 (s, 3H), 1.25 (d, J=7.3, 3H).

1. concentrationconcentrated in vacuo
2. dissolutionThe resulting white solid was dissolved in water
3. extractionThe resulting solutions was extracted with ethyl acetate (3×100 mL)
4. dry with materialthe combined organic phase was dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-d81ca40a9f334394a4fd8061926c94e5

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08735398B2