Water → 1-Benzyl-5-(3-tert-butoxycarbonylaminomethylphenyl)-7-chloro-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid

To a solution of 2-benzylamino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.91 g) in acetic acid ethyl ester (10 ml) were added water (4 ml) and a 1N aqueous solution of sodium hydroxide (3 ml). To the mixture was added monoethyl fumarate ester chloride (330 mg), which was stirred for one hour under ice-cooling. To the mixture was added acetic acid ethyl ester (30 ml). The organic layer was washed with water and dried over anhydrous MgSO41 followed by distilling off the solvent. The residue was dissolved in ethanol (10 mL), to which was added potassium carbonate (400 mg). The mixture was stirred overnight at room temperature. Insolubles were filtered off, and the solvent was distilled off. The residue was purified by means of a silica gel column chromatography to give ethyl ester of 1-benzyl-5-(3-tert-butoxycarbonylaminomethylphenyl)-7-chloro-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid (1.06 g).

1. temperaturecooling
2. washThe organic layer was washed with water
3. customdried over anhydrous MgSO41
4. distillationby distilling off the solvent
5. dissolutionThe residue was dissolved in ethanol (10 mL), to which
6. additionwas added potassium carbonate (400 mg)
7. stirringThe mixture was stirred overnight at room temperature
8. filtrationInsolubles were filtered off
9. distillationthe solvent was distilled off
10. customThe residue was purified by means of a silica gel column chromatography

ORD record

ord-e660761dfded4330889fd11ee1f0b43c

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06352982B1