1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-[(2E,4E,6E,8E]-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoylamino)-5-hydroxyphenyl butanoate

Participants

Reaction Steps

To a solution of EDCI (0.023 g, 0.12 mmol) in anhydrous DMF (5 mL) was added a solution of retinoic acid (0.031 g, 0.10 mmol) in anhydrous DMF (5 mL). The mixture was stirred at room temperature for 0.5 h. A solution of 2-amino-5-hydroxy-phenyl butanoate (KCBG05, 0.020 g, 0.12 mmol) and DMAP (cat.) in anhydrous DMF (2 mL) was added to the mixture, and again stirred for 4 h. The reaction was quenched with NH4Cl (aq.), extracted with EtOAc (2×30 mL). The extracts were washed with H2O (2×30 mL), dried over anhydrous Na2SO4, and evaporated. The residue was purified by flash column chromatography over silica gel (EtOAc:hexane=1:6) to give 2-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoylamino]-5-hydroxyphenyl butanoate (KCBG10, 0.038 g, 78%) as a yellow solid.

Provenance & Evidence