Triethylamine → 2-{(R)-1-[N-Toluoyl-(3-Phthalimido-2-oxo-propyl)amino]-2-methyl-propyl}-3-benzyl-7-chloro-3H-quinazolin-4-one

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Reaction Steps

To 2-[(R)-1-(3-phthalimido-2-oxo-propylamino)-2-methyl-propyl]-3-benzyl-7-chloro-3H-quinazolin-4-one (7.22 g, 13.3 mMol) in CH2Cl2 (50 mL) was added Et3N (2.0 mL, 14.3 mMol) and toluoyl chloride (1.9 mL, 14.4 mMol). The reaction was stirred at RT for 18 h, concentrated under vacuum, taken up in EtOAc, washed with 1 N HCl, brine, dried (MgSO4) and evaporated to dryness. Purification by flash chromatography on silica gel (1% MeOH/CH2Cl2) followed by trituration with (1:1) Et2O/pet. ether, filtration and drying under vacuum gave the title compound (6.41 g, 73%) as a white solid. A side fraction (1.20 g) which contained mostly product was also obtained: 1H NMR (400 MHz, CDCl3) δ 8.23 (d, J=8.6 Hz, 1H), 7.69–7.78 (m, 5H), 7.45–7.49 (m, 3H), 7.34 (t, 2H), 7.25–7.29 (m, 3H), 7.15 (d, J=8.1 Hz, 2H), 6.19 (d, J=15.9 Hz, 1H), 5.82 (d, J=10.6 Hz, 1H), 5.12 (d, J=15.9 Hz, 1H), 4.56 (d, J=18.8 Hz, 1H), 4.26 (d, J=18.8 Hz, 1H), 4.09 (d, J=17.6 Hz, 1H), 3.90 (d, J=17.6 Hz, 1H), 2.62 (m, 1H), 2.42 (s, 3H), 0.93 (d, J=6.8 Hz, 3H), 0.32 (d, J=6.4 Hz, 3H); MS (ES) m/e 661.2 (M+H)+.

Provenance & Evidence