Acetic Acid → HCID 18697818, compound

To a solution of diisopropylamine (1.1 ml, 7.70 mmol) in tetrahydrofuran (12 ml) was added, at -78° C. under an argon atmosphere, 1.5 N butyllithium (4.8 ml, 7.22 mmol). The mixture was stirred for 30 min. Ethyl propiolate (0.9 ml, 8.66 mmol) and a solution of 4-acetylamino-2-nitrobenzaldehyde (1.0 g, 4.81 mmol) in tetrahydrofuran (6 ml) were added in that order, and the mixture was further stirred at -78° C. for one hr. A solution of acetic acid (0.9 ml, 14.91 mmol) in tetrahydrofuran (3 ml) was then added thereto, followed by extraction with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, water, a saturated aqueous sodium bicarbonate solution, and saturated brine in that order. It was then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give ethyl 4-hydroxy-4-(4-acetylamino-2-nitrophenyl)-2-butynoate (1.613 g) as an oil. Ethyl 4-hydroxy-4-(4-acetylamino-2-nitrophenyl)-2-butynoate thus prepared was dissolved in toluene (14 ml), 4-methoxybenzylazide (2.35 g, 14.4 mmol) was added to the solution, and the mixture was stirred at 10° C. for 18 hr. The reaction mixture was cooled to room temperature, and the resultant crystal as a precipitate was collected by suction filtration to give a 3:1 mixture (1.09 g, 48%) of ethyl 4-hydroxy-(4-acetylamino-2-nitrophenyl)methyl-1-(4-methoxybenzyl)-1,2,3-triazole-5-carboxylate (a-1) and ethyl 5-hydroxy-(4-acetylamino-2-nitrophenyl)methyl-1-(4-methoxybenzyl)-1,2,3-triazole-4-carboxylate (a-2).

1. stirringthe mixture was further stirred at -78° C. for one hr
2. extractionfollowed by extraction with ethyl acetate
3. washThe organic layer was washed with dilute hydrochloric acid, water
4. dry with materialIt was then dried over anhydrous magnesium sulfate
5. customThe solvent was removed under reduced pressure

ORD record

ord-aa57f914c1fb4ecc9f0ee41a881bff63

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06093714