Hydrochloric Acid → HCID 178457660, compound

To a solution of methyl 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoate (16.4 g) in THF (160 mL) was added methanol (35 mL) and 4N-NaOH (35 mL) at 60° C. The mixture was stirred for 2 h, neutralized with conc.HCl. The mixture was concentrated, diluted with water and extracted with ethyl acetate. The extract was concentrated to give crude mixture of 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoic acid. To a solution of the crude mixture was added isopropylamine (3.95 mL), 1-hydroxybenzotriazole (5.33 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (6.67 g) and diisopropylethylamine (6.0 mL) under ice cooling. The mixture was stirred at room temperature for 14 h, diluted with water and extracted with ethyl acetate. The extract was washed with brine, concentrated. The residue was crystallized from ethyl acetate to give the titled compound (16.7 g) as a colorless powder.

1. concentrationThe mixture was concentrated
2. additiondiluted with water
3. extractionextracted with ethyl acetate
4. concentrationThe extract was concentrated
5. customto give crude
6. stirringThe mixture was stirred at room temperature for 14 h
7. extractionextracted with ethyl acetate
8. washThe extract was washed with brine
9. concentrationconcentrated
10. customThe residue was crystallized from ethyl acetate

ORD record

ord-f4e94f0c83bd4b1b9571d447842c8c44

Source dataset

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06649643B1