di-tert-butyl N-(4-nitro-2-fluorobenzoyl)-(L)-glutamate → 4-Amino-2-fiuorobenzoylglutamic acid di-t-butyl ester

Beteiligte Stoffe

Reaktionsschritte

A solution of di-tert-butyl-N (4-nitro-2-fluorobenzoyl)-(L)-glutamate (3.6 g, 8.4 mmoles) in 95% ethanol (100 mL) was mixed with 10% palladium on carbon (0.25 g) and placed on a Parr apparatus. The mixture was shaken under hydrogen atmosphere for 2 hours. The reaction mixture was filtered, spin evaporated, and dried to give a white solid, di-tert-butyl N-(4-amino-2-fluorobenzoyl)-(L)-glutamate yield, 3.0 g (91%); mp 91°-95° C.; 1H-NMR (CDCl3) δ 1.41 (s, 9H), 1.48 (s, 9H), 2.0-2.4 (m, 4H), 2.8 (br s, 2H), 4.71 (m, 1H), 6.34 (d, 1H), 6.48 (d, 1H), 7.17 (q, 1H), 7.86 (t, 1H); uv (MeOH) 280 nm max (16800), 238 min (2760), 212 sh (12100); mass spec (CI) m/e 397 (21 %), 341 (13), 285 (100).

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