Hydrochloric Acid → HCID 86653406, compound

Participants

Reaction Conditions

Reaction Steps

LiOH (13 mg, 0.54 mmol) in water (2 mL) was added to 4 (384 mg, 0.36 mmol) in THF (8 mL) at 0° C. After 1.5 h of stirring at 0° C. the reaction mixture was neutralized with aqueous 0.5 M HCl then brine (50 mL) and EtOAc (50 mL) were added. The phases were separated and the aqueous phase was extracted with EtOAc (3×10 mL). The organic phases were combined, dried over MgSO4, filtered then concentrated under reduced pressure. The crude product was dried under high vacuum before to be use for the next step. The crude carboxylic acid in CH2Cl2/THF (250 mL, 12:1 v/v) was added dropwise over a period of 3 h to 2-methyl-6-nitrobenzoic anhydride (149 mg, 0.43 mmol) and 4-(dimethylamino)pyridine (105 mg, 0.86 mmol) in CH2Cl2 (120 mL) at rt under Ar(g). After 19 h the reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography eluting with CH2Cl2/CH3OH (100:2 then 100:10) to yield 5 as a white solid (203 mg, 54%).

Provenance & Evidence