Sodium Hydroxide → HCID 18457823, compound

Methyl 6′-methyl-3′-[(propylamino)carbonyl]-1,1′-biphenyl-4-carboxylate (216 mg, 0.7 mmol) in methanol (4 ml) was mixed with aqueous sodium hydroxide (2N, 1 ml) and stirred at room temperature for 2 h. The methanol was evaporated, the reaction diluted with water (4 ml) and extracted with chloroform (2×5 ml). The aqueous was acidified with hydrochloric acid (2N, 2 ml) and extracted with chloroform (2×6 ml). Both sets of organic extracts were combined in methanol (4 ml) and stirred with aqueous sodium hydroxide (2N, 2 ml) for 3 h. The methanol was evaporated, the reaction diluted with water (4 ml) and washed with chloroform (2×5 ml). The aqueous was acidified with hydrochloric acid (2N, 2 ml) and extracted with chloroform (2×6 ml). The solvent was evaporated from the organic extracts to give 6′-methyl-3′-[(propylamino)carbonyl]-1,1′-biphenyl-4-carboxylic acid (121 mg). NMR: δH CDCl3 8.13, (2H, d), 7.69, (1H, dd), 7.62, (1H, d), 7.41, (2H, d), 7.35, (1H, d), 3.42, (2H, t), 2.30, (3H, s), 1.64, (2H, m), 0.99, (3H, t).

1. customThe methanol was evaporated
2. additionthe reaction diluted with water (4 ml)
3. extractionextracted with chloroform (2×5 ml)
4. extractionextracted with chloroform (2×6 ml)
5. stirringstirred with aqueous sodium hydroxide (2N, 2 ml) for 3 h
6. customThe methanol was evaporated
7. additionthe reaction diluted with water (4 ml)
8. washwashed with chloroform (2×5 ml)
9. extractionextracted with chloroform (2×6 ml)
10. customThe solvent was evaporated from the organic extracts

ORD record

ord-5db5183355f74270941034757d4860fb

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07208629B2