N-Methylbenzylamine → HCID 28168303, compound

To a-30° C. solution of N-t-Boc-L-alanine (20.0 g, 0.106 mol) and triethylamine (16.8 mL, 0.119 mol) in THF (300 mL) was added isobutyl chloroformate (15.0 mL, 0.114 mol) drop wise. The reaction mixture was warmed to ambient temperature over 1.25 h and then stirred for 3.5 h. The reaction mixture was cooled to 0° C. and a solution of N-methylbenzylamine (14.3 mL, 0.111 mol) and triethylamine (18.8 mL, 0.134 mol) in THF (60 mL) was added drop wise. The reaction mixture was allowed to warm to ambient temperature. After 16 h, saturated NaHCO3 (200 mL) was added and most of the THF was removed under reduced pressure. The remaining aqueous layer was extracted with EtOAc (2×250 mL). The combined organic layers were washed with brine (100 mL), dried (Na2SO4) and concentrated under reduced pressure. Purification by column chromatography (silica gel, 10% EtOAc in hexanes to 40% EtOAc in hexanes) gave (S)-tert-butyl 1-(benzyl(methyl)amino)-1-oxopropan-2-ylcarbamate (26.3 g, 85%) as a colorless oil. 1H NMR consistent.

1. temperatureThe reaction mixture was cooled to 0° C.
2. temperatureto warm to ambient temperature
3. waitAfter 16 h
4. customwas removed under reduced pressure
5. extractionThe remaining aqueous layer was extracted with EtOAc (2×250 mL)
6. washThe combined organic layers were washed with brine (100 mL)
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated under reduced pressure
9. customPurification by column chromatography (silica gel, 10% EtOAc in hexanes to 40% EtOAc in hexanes)

ORD record

ord-31409f75c403481f8fd6d301f3b17c0f

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07863271B2