Hydrochloric Acid → HCID 86653401, compound

Participants

Reaction Conditions

Reaction Steps

LiOH (9 mg, 0.37 mmol) in water (2 mL) was added to 4 (255 mg, 0.25 mmol) in THF (8 mL) at 0° C. After 45 minutes of stirring at 0° C. the reaction mixture was neutralized with aqueous 0.5M HCl, then brine (40 mL) and EtOAc (40 mL) were added. The phases were separated and the aqueous phase was extracted with EtOAc (20 mL). The organic extracts were combined, dried over MgSO4, filtered then concentrated under reduced pressure. The crude product was dried under high vacuum before being used in the next step. The crude carboxylic acid in CH2Cl2/THF (200 mL, 12:1 v/v) was added dropwise over a period of 3 h to 2-methyl-6-nitrobenzoic anhydride (103 mg, 0.30 mmol) and 4-(dimethylamino)pyridine (73 mg, 0.60 mmol) in CH2Cl2 (50 mL) at rt under Ar(g). After 15 h, the reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography eluting with CH2Cl2/isopropanol (100:2.5 then 100:5) to yield 5 as a white solid (117 mg, 47%).

Provenance & Evidence