Methyl iodide → N-(tert-Butoxycarbonyl)-N-methyl-D-alanine

To 48 ml of a solution of Boc-D -Ala-OH (3.0 g, 15.9 mmol) in tetrahydrofuran (THF) was added 60% sodium hydride (1.9 g, 47.6 mmol) under ice-cooling and the mixture was stirred for 10 minutes. Then, methyl iodide (7.9 ml, 127 mmol) was added and the mixture was further stirred at room temperature for 22 hours. The reaction mixture was then concentrated under reduced pressure, ice-cooled, acidified with 10% citric acid-H2O, and extracted with ethyl acetate. The extract was washed with saturated NaCl-H2O, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from hexane and the crystal crop was washed with hexane to provide the title compound. Yield 3.07 g (94.8%).

1. temperaturecooling
2. stirringthe mixture was further stirred at room temperature for 22 hours
3. concentrationThe reaction mixture was then concentrated under reduced pressure, ice-
4. temperaturecooled
5. extractionextracted with ethyl acetate
6. washThe extract was washed with saturated NaCl-H2O
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was crystallized from hexane
10. washthe crystal crop was washed with hexane

ORDレコード

ord-b8bc3247e8784172a873f1c3fe794e9a

出典データセット

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05698670