Hydrochloric Acid → HCID 23297331, compound

Temperature

80 °C

N-Succinimidyl 3,4-bis(methoxycarbonyloxy)-phenylacetate (500 mg, 1.76 mmol) and 4-hydroxy-3-methoxybenzylamine hydrochloride were dissolved in 20 ml of 1,4-dioxane and 20 ml of water under nitrogen, and sodium hydrogencarbonate (148 mg, 1.76 mmol) was added. The mixture was heated at 80° C. for 2 h, treated with further sodium hydrogen carbonate (325 mg, 3.87 mmol), stirred for a further 1 h at 80° C. and left to cool. The orange-red mixture was acidified using hydrochloric acid (5%) and extracted with ethyl acetate. The organic phase was washed with saturated NaCl solution, dried over Na2SO4 and filtered, and the filtrate was evaporated under reduced pressure. The residue was purified by chromatography on silica gel using the eluent ethyl acetate. Yield of N-(4-hydroxy-3-methoxybenzyl)-3,4-dihydroxyphenylacetamide 340 mg (63% of theory).

1. waitleft
2. temperatureto cool
3. extractionextracted with ethyl acetate
4. washThe organic phase was washed with saturated NaCl solution
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. customthe filtrate was evaporated under reduced pressure
8. customThe residue was purified by chromatography on silica gel using the eluent ethyl acetate

ORD record

ord-b27a2a58f71d48469af1f7ee71c92e6c

Source dataset

uspto-grants-2000_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06117365