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. Author manuscript; available in PMC: 2021 Oct 19.
Published in final edited form as: ACS Appl Bio Mater. 2020 Sep 17;3(10):6944–6958. doi: 10.1021/acsabm.0c00823

Scheme 2. Synthetic route for small molecule coumarin-carbamate-PEG4-azide (CMR-azide).

Scheme 2.

Reagents and conditions as follows: a) dimethylformamide dimethyl acetal in DMF under reflux; b) sodium periodate in 1:1 THF to DI water at room temperature; c) propargyl zinc bromide in THF at 0 °C; d) ethyl 4-azidobutanoate, CuSO4, and sodium ascorbate in 9:1 methanol to DI water at room temperature; e) 4-nitrophenyl chloroformate, anhydrous pyridine, and DMAP in anhydrous DCM at 0 °C; f) azido-tetraethyleneglycol-amine, anhydrous pyridine, and DMAP in anhydrous DCM at 0 °C to room temperature; and g) LiOH in 2:1 THF to DI water at room temperature.