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. 2021 Aug 23;64(17):12938–12963. doi: 10.1021/acs.jmedchem.1c01094

Scheme 3. Representative Synthetic Scheme for the Preparation of 4-Cyano-phenylpropenyl Compounds with Different Substitutions of the Amino Acid Side Chain.

Scheme 3

Shown for compound 21a bearing an extended linker to the amino acid moiety. Reagents and conditions are as follows: (a) aldehyde 15u, NaBH(OAc)3, AcOH, DCE, rt, overnight (81%); (b) aldehyde 19a, NaBH(OAc)3, AcOH, DCE, rt, overnight (81%); (c) TFA, CH2Cl2, H2O, rt, 2 h, (86%). The variable group in compounds 19b–k, 20b–k, and 21b–k is indicated in blue.