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. 2023 Jun 16;66(13):8600–8613. doi: 10.1021/acs.jmedchem.3c00258

Scheme 1. Synthetic Procedure for p-COOH-Bn-DO3AiBu(tBu)3.

Scheme 1

Reagents and conditions: (a) isobutylaldehyde, sodium triacetoxyborohydride, THF, rt for 24 h, 42.4%; (b) (1) 1 M BH3-THF, THF, 0 °C for 1 h, reflux for 24 h, 0 °C for 1 h, (2) conc. HCl, rt for 24 h, 74.7%; (c) tert-butyl bromoacetate, Na2CO3, acetonitrile, reflux for 24 h, 58.8%; (d) Pd(OAc)2, 1,2-bis(diphenylphosphino)ethane, TEA, CO (1 atm), benzyl alcohol, DMF, 80 °C for 24 h, 25.5%; (e) 10% Pd/C, H2 (1 atm), methanol, rt for 5 h, 48.8%.