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Reagents and conditions: (i) MeOH, SOCl2, 0 °C to rt, 4–6 h; (ii) octanoic acid, NMM, anhydrous DCM, EDC.HCl, 6 h, rt; (iii) NMM, anhydrous DCM, EDC.HCl, HOBt, 6–8 h, 0 °C to rt; (iv) NaOH (2 N), MeOH, 5–8 h, rt; (v) 25% TFA in DCM, 2 h, rt; (vi) NMM, anhydrous DCM, HBTU, HOBt, 24 h, 0 °C to rt; (vii) anhydrous THF, LiBH4, 12 h, 0 °C to rt.
