Dicyclohexylcarbodiimide → HCID 118193044, compound

Participants

Reaction Steps

6 ml (0.042 mol) of TEA was added to a mixture of 4.2 g (0.14 mol) of (3R)-4-(Toluene-4-sulfonyl)-thiomorpholine-3-carboxylic acid, 3.0 g (0.017 mol) of L-leucine ethyl ester hydrochloride, 3.2 g (0.014 mol) of DCC, and 1.7 g (0.014 mol) of DMAP in 200 ml of CH2Cl2, and the mixture was reacted at room temperature for 24 h. After the reaction, the solid was removed by sucking filtration, the solvent was removed by evaporation, the residue was dissolved with an appropriate amount of ethyl acetate, filtered to remove the insoluble matter, diluted with ethyl acetate, successively washed with 10% of NaHCO3 solution and saturated NaCl solution, dried with Na2SO4. The drying agent was removed, ethyl acetate was removed by evaporation, the residue was separated by flash chromatographic column (eluent: CH2Cl2:CH3Cl=1:1), to obtain 4.0 g of oily matter. 1H-NMR (400 MHz, CDCl3): δ 7.77237-7.74077 (m, 2H), 7.36382 (d, 2H, J=7.988 Hz), 6.74090 (d, 1H, J=9.244 Hz), 4.80098-4.77466 (m, 1H), 4.68244-4.58898 (m, 1H), 4.28174-4.15708 (m, 3H), 3.53789-3.28674 (m, 1H), 3.13092 (d, 1H, J=13.676), 2.56954-2.42247 (m, 5H), 2.24620-2.20545 (m, 1H), 1.66352-1.53450 (m, 3H), 1.30702-1.26745 (m, 3H), 0.96159-0.91891 (m, 6H); MS (EI) m/z: 443.1, 397.1, 369.1, 287.1, 256.0, 213.1, 155.0, 139.0, 112.0, 91.0, 65.0.

Provenance & Evidence