Water → HCID 10704342, compound

To a solution of 2-nitrobenzyl bromide (1.0 g, 4.63 mmol) and glycine methyl ester hydrochloride (868 mg, 6.94 mmol) in dry DMF (10 mL), was added DIPEA (2.42 mL, 13.89 mmol) under nitrogen atmosphere. The reaction mixture was stirred at. r.t. overnight. After completion of the reaction as confirmed by TLC, water (50 mL) was added to the reaction mixture. The crude product was extracted with ethyl acetate (20 mL). The aqueous layer was washed with ethyl acetate (2×10 mL), The combined organic extract was dried over Na2SO4 and the solvents were removed in vacuo to afford the crude compound, which was purified by column chromatography (silica gel, 1:9 EtOAc:Pet Ether) to afford pure (2-nitro-benzylamino)-acetic acid methyl ester (765 mg 73%) as a viscous oil.

1. customr.t. overnight
2. customAfter completion of the reaction
3. additionwas added to the reaction mixture
4. extractionThe crude product was extracted with ethyl acetate (20 mL)
5. washThe aqueous layer was washed with ethyl acetate (2×10 mL)
6. extractionThe combined organic extract
7. dry with materialwas dried over Na2SO4
8. customthe solvents were removed in vacuo
9. customto afford the crude compound, which
10. customwas purified by column chromatography (silica gel, 1:9 EtOAc:Pet Ether)

ORD record

ord-1ce005cc46064d3e81e3dd2c22e03302

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455479B2