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. 2020 Feb 10;63(5):2588–2619. doi: 10.1021/acs.jmedchem.9b01526

Scheme 6. Synthesis of Compound 10d.

Scheme 6

Reagents and conditions: (a) TEA (5.0 equiv), anhydrous DCM, methanesulfonyl chloride 122 (2.0 equiv), rt, 48 h, yield 82%; (b) MeOH/THF (1:1 v/v), 2 M LiOH, rt, 16 h, yield 82%; (c) HOBt (1.1 equiv), EDC (1.1 equiv), TEA (2.2 equiv), DCM, rt, 16 h, yield 15%.