Sodium hydride → HCID 54140711, compound

Temperature

0 °C

To a solution of (2S)-3-hydroxy-2-t-butoxycarbonylaminopropanoic acid (10.11 g) in dimethylformamide (200 ml, abbreviated as DMF), sodium hydride (60%, 3.95 g) was added under cooling with ice. The mixture was stirred for 30 minutes at 0° C. To the reaction mixture, (bromomethyl)cyclohexane (9.0 ml) was added at a dropwise under cooling with ice. Tetra-n-butylammonium iodide (910 mg) was added thereto. The mixture was stirred for 23 hours at room temperature. In addition, to the reaction mixture, (bromomethyl)cyclohexane (2.1 ml) was added at a dropwise. The mixture was stirred for 4 hours. Again, (bromomethyl)cyclohexane (2.1 ml) was added at a dropwise thereto. The mixture was stirred for 25 hours at room temperature. After the concentration of reaction mixture, the residue was diluted with 1N—HCl and extracted with ethyl acetate. The extract solution was washed by water and saturated solution of sodium chloride successively, dried over anhydrous sodium sulfate and concentrated. The residue was purified with column chromatography on silica gel (chloroform:methanol=97:3) to obtain the title compound (2.52 g) having the following physical data.

1. temperatureunder cooling with ice
2. temperatureunder cooling with ice
3. stirringThe mixture was stirred for 23 hours at room temperature
4. stirringThe mixture was stirred for 4 hours
5. stirringThe mixture was stirred for 25 hours at room temperature
6. customAfter the concentration of reaction mixture
7. extractionextracted with ethyl acetate
8. washThe extract solution was washed by water and saturated solution of sodium chloride successively
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated
11. customThe residue was purified with column chromatography on silica gel (chloroform:methanol=97:3)

ORD record

ord-5b32672c21ba4f46aad87c79187fddac

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06605608B1