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. 2024 May 23;67(11):9124–9149. doi: 10.1021/acs.jmedchem.4c00268

Scheme 3. Synthesis of Final Compounds CPK5 and CPK10.

Scheme 3

Reagents and conditions: (a) 4-Chlorobenzoyl chloride, DIPEA, DCM, 2 h, RT; (a′) 4-chlorobenzenesulfonyl chloride, DIPEA, DCM, 2 h, RT; (b) TFA/DCM (1/3, v/v), triisopropylsilane, 3 h, RT; (c) Boc-l-Tyr(2-Br-Z)–OH, HOBt, HBTU, DIPEA, DCM/DMF (4/1, v/v), RT, overnight; (c′) Boc-l-Tyr(tBu)–OH, HOBt, HBTU, DIPEA, DCM/DMF (4/1, v/v), RT, overnight; (d) TFA/DCM (1/5, v/v), triisopropylsilane, 2 h, RT; (e) 4-bromobenzyl bromide, potassium tert-butoxide, DMF, 130 °C, overnight.