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With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;
General procedure: To a round-bottom flask was added acid (8.0 mmol, 1.0 equiv.), methoxyamine hydrochloride (12 mmol, 1.5 equiv.), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 12 mmol, 1.5 equiv), the mixture was well stirred in dry CH2Cl2 (24 mL), then N,N-dimethylpyridin-4-amine (DMAP, 24 mmol, 3.0 equiv) was added, the reaction was allowed to stir for overnight. Then the reaction was quenched with water and extracted with EtOAc. The organic layer was combined and dried over anhydrous sodium sulfate. After filtration and concentration, the residue was applied to a flash column chromatography to give 1.58 g of d in 71% yield as white solid.
With water; sodium hydroxide; In methanol; at 50.0℃;
General procedure: A NaOH aqueous solution (30 mL, 1 M) was added to a stirring mixture of the desired ester (8.5 mmol) in MeOH (30 mL) under air atmosphere. The reaction mixture was heated to 50 C, observing complete hydrolysis by TLC after 30 min. The reaction mixture was concentrated under reduced pressure. The residue was quenched with 6 M HCl until pH < 3 and solid precipitation, then filtered to give 1.9 g of c in 89% yield as white solid.
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