4-Methylmorpholine → 2-(Phenylamino)acetamide

Beteiligte Stoffe

Reaktionsschritte

To a solution of acid 9 (38 mg, 0.039 mmol) and N-methyl morpholine (4.5 μL, 0.041 mmol) in 1.5 mL of anhydrous THF cooled to 0° C. was added isobutyl chloroformate (5.2 μL, 0.040 mmol) and the mixture was stirred for 1 hour at that temperature. A solution of D-phenylglycinamide (8.6 mg, 0.057 mmol) and Et3N (10 μL) in 1 mL of THF/H2O 4:1 was added and the mixture was stirred for 1 h at 0° C. and 1 h at room temperature. After removal of the THF under vacuum, the residue was suspended in H2O (5 mL) and extracted with EtOAc (5 mL×3). The combined organic layers were dried over Na2SO4 and filtered. The solvent was removed under vacuum and the residue was purified by chromatography on a silica gel column (5-8% MeOH in CH2Cl2) to give conjugate S1 (28 mg, 66%) as a white solid: 1H NMR (600 MHz, DMSO-d6) δ8.41 (d, J=7.9 Hz, 1H), 8.31 (t, J=5.3 Hz, 3H), 7.65 (br. s., 1H), 7.25-7.45 (m, 14H), 7.13 and 7.12 (2×s, 2H), 5.36 (d, J=8.2 Hz, 1H), 3.11-3.17 (m, 6H), 2.35-2.48 (m, 2H), 2.30-2.34 (m, 2H), 2.28 (s, 9H), 2.21 (s, 9H), 1.58-1.67 (m, 6H), 1.37-1.44 (m, 6H); HRMS (ESI) calcd. for C55H63N6O18 (M+H)+: 1095.4193, found 1095.4203.

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