Methyl iodide → N-Cbz-N-methyl-L-leucine

To a solution of N-Cbz-leucine (1.38 g, 5.2 mmol) in THF (15 mL) at 0° C. was added methyl iodide (2.5 mL, 40.1 mmol). Sodium hydride (60% dispersion in oil, 0.6 g, 15 mmol) was added cautiously, and the resultant mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with EtOAc (25 mL) and water (2 mL) was added dropwise. The mixture was concentrated to dryness, and the residue was partitioned between ether (15 mL) and water (50 mL). The organic layer was extracted with saturated aqueous NaHCO3 (25 mL), and the combined aqueous extracts were acidified to pH 2 with 3 N HCl. The product was extracted with EtOAc (3×25 mL), dried over MgSO4, filtered, and concentrated to afford the title compound (1.41 g) as a yellow solid.

1. additionwas added dropwise
2. concentrationThe mixture was concentrated to dryness
3. customthe residue was partitioned between ether (15 mL) and water (50 mL)
4. extractionThe organic layer was extracted with saturated aqueous NaHCO3 (25 mL)
5. extractionThe product was extracted with EtOAc (3×25 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-b2d01a0a30fc4e8e9793cba17070e42f

Source dataset

uspto-grants-2000_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06066730