Methanol → Methyl 2-amino-3-(4-nitrophenyl)propanoate

2-Amino-3-(4-nitrophenyl)propionic acid (4.60 g, 21.9 mmol) was added to a mixed solution of methanol (100 ml) and chloroform (50 ml), and sulfuric acid (3 ml) was added, which was followed by refluxing under heating for 30 hours. The reaction mixture was concentrated under reduced pressure and water was added to the residue. The pH was adjusted to 8-9 with a 1N aqueous sodium hydroxide solution and the mixture was extracted with chloroform. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. After filtration, low boiling matters were distilled away from the filtrate under reduced pressure to give 4.06 g of methyl 2-amino-3-(4-nitrophenyl)propionate as a yellow oil (83%). This oil (4.00 g, 17.8 mmol) was dissolved in acetonitrile (56 ml), and pyridine (1.76 ml, 21.4 mmol) and n-butylsulfonyl chloride (2.80 g, 17.8 mmol) were sequentially added, which was followed by stirring at 70° C. for 4.5 hours. After cooling, the reaction mixture was poured into water (70 ml) and extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. After filtration, low boiling matters were distilled away from the filtrate under reduced pressure to give 4.06 g of methyl 2-(n-butylsulfonylamino)-3-(4-nitrophenyl)propionate as an orange oil (66%). This oil (3.40 g, 9.88 mmol) was dissolved in acetic acid (130 ml) and 10% palladium-carbon (1.5 g) was added. The mixture was stirred for 3 days under a hydrogen atmosphere. The reaction mixture was filtered through Celite and acetic acid was distilled away from the filtrate under reduced pressure to quantitatively give 3.16 g of methyl 3-(4-aminophenyl)-2-(n-butylsulfonylamino)propionate as a brown solid.

1. additionwas added
2. temperatureby refluxing
3. temperatureunder heating for 30 hours
4. concentrationThe reaction mixture was concentrated under reduced pressure and water
5. additionwas added to the residue
6. extractionthe mixture was extracted with chloroform
7. washThe extract was washed with water and saturated brine
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationAfter filtration, low boiling matters
10. distillationwere distilled away from the filtrate under reduced pressure

ORD record

ord-3eb1caac6dce4090b1a95e7297b00e30

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05753670