Triethylamine → Benzyl 2-(2,4-dinitrobenzamido)acetate

To a solution of benzyl glycinate.PTS salt (1.589 g, 4.716 mmol) in chloroform (20 mL) was added triethylamine (1.95 mL, 14. 148 mmol) at ice cold temperature. A solution of 2,4-dinitrobenzoyl chloride (prepared from 2,4-dinitrobenzoic acid, 1.0 g and SOCl2, 10 mL, refluxed for 2 h and evaporated the solvents) in chloroform (5 mL) was added to the above solution for 10 min and stirred for 1 h. After completion of the reaction, it was diluted with chloroform (100 mL). The chloroform layer was washed with water (2×50 mL), brine (50 mL) and dried over anhyd Na2SO4. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using chloroform:methanol (98:02) as eluents to give the product as an off-white color solid (1.55 g, 92%), mp 116-118° C. 1H NMR (400 MHz, CDCl3): δ 8.91 (1H, d, J=2.0 Hz), 8.52 (1H, dd, J=8.2, 2.2 Hz), 7.77 (1H, d, J=8.4 Hz), 7.38 (5H, s), 6.52-6.55 (1H, m), 5.24 (2H, s), 4.31 (2H, d, J=5.2 Hz); LC-MS (negative ion mode): m/z 358 (M−H)−.

1. temperaturerefluxed for 2 h
2. customevaporated the solvents) in chloroform (5 mL)
3. additionwas added to the above solution for 10 min
4. customAfter completion of the reaction, it
5. washThe chloroform layer was washed with water (2×50 mL), brine (50 mL)
6. dry with materialdried over anhyd Na2SO4
7. filtrationThe solution was filtered
8. customevaporated the solvent
9. customThe residue was chromatographed over silica gel column

ORD record

ord-ddba9c63515e40d8ad0ee3727d13a6f6

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08906344B2