Triethylamine → 3-[(tert-Butoxycarbonyl)amino]benzyl Methanesulfonate

Temperature

-50 °C

1-[3-[(tert-Butoxycarbonyl)amino]phenyl]methanol (10 g, 44.8 mmoles) (Ref.: F. J. Brown, P. R. Bernstein, L. A. Cronk, D. L. Dosset, K. C. Hebbel. T. P. Maduskuie, Jr., H. S. Shapiro, E. P. Vacek, Y. K. Lee, A. K. Willard, R. D. Krell and D. W. Snyder, J. Med. Chem., 32, 1989, 807-826) and triethylamine (13 g, 17.9 mL, 138.4 mmoles) were dissolved in anhydrous THF (169 mL) and the solution was stirred and cooled to −50° C. Methanesulfonyl chloride (10.26 g, 7.02 mL, 89.6 mmoles) in anhydrous THF (85 mL) was added dropwise over a period of 20 min at −50° C. under an argon atmosphere. The mixture was stirred at −50° C. for an additional 20 min. A saturated aqueous solution of ammonium chloride (12.9 g) was added and the mixture was warmed to 25° C. The mixture was filtered and the filtrate was extracted twice with ethyl acetate. The ethyl acetate was washed with brine, water, dried (MgSO4), filtered and evaporated to dryness to give the title compound (14.78 g). The material was used without further purification.

1. stirringThe mixture was stirred at −50° C. for an additional 20 min
2. temperaturethe mixture was warmed to 25° C
3. filtrationThe mixture was filtered
4. extractionthe filtrate was extracted twice with ethyl acetate
5. washThe ethyl acetate was washed with brine, water
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customevaporated to dryness

ORD record

ord-2ad6c94e641c4452b00bb37a872b2b8d

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07635697B2