[CH3:1][CH:2]1[C:7]([CH:9]=[O:10])([CH3:8])[CH2:6][CH2:5][CH:4]=[CH:3]1.[CH3:11][O:12][C:13](=[O:21])[CH:14]([CH2:19][OH:20])[NH:15][CH:16]([CH3:18])[CH3:17].ClC1C=CC=C(Cl)C=1C(O)=O.O>C1(C)C=CC=CC=1>[CH3:1][CH:2]1[C:7]([CH:9]=[O:10])([CH3:8])[CH2:6][CH2:5][CH:4]=[CH:3]1.[O:12]1[CH2:13][CH2:14][NH:15][CH2:16]1.[CH3:11][O:12][C:13](=[O:21])[CH:14]([CH2:19][OH:20])[NH:15][CH:16]([CH3:18])[CH3:17]A solution of triplal (2, 1.0 equiv), N-isopropyl-DL-serine methyl ester (1, 1.05 equiv) and 2,6-dichlorobenzoic acid (0.01 equiv) is refluxed 6 hours in toluene during which time water is removed by azeotropic distillation. The solution is cooled, washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, and filtered. The toluene is subsequently removed under reduced pressure to yield the desired product, 3.
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