Triethylamine → HCID 7843604, compound

Participants

Reaction Steps

To a mixture of O-benzylglycine p-toluenesulfonic acid salt (6.41 g) and triethylamine (4.04 g) in methylene chloride (100 ml) was added portionwise 3-nitrobenzoyl chloride (3.71 g) under cooling in an ice-bath and stirring. The resultant mixture was stirred for 1 hour under the same condition and for 1 hour further at ambient temperature. From the reaction mixture, methylene chloride was removed in vacuo and to the residue were added water and ethyl acetate with stirring. The separated organic layer was washed with diluted hydrochloric acid, aqueous sodium bicarbonate and water twice respectively. The extract was dried over magnesium sulfate and evaporated in vacuo to give N-(3-nitrobenzoyl)glycine benzyl ester (5.98 g). 1H-NMR (CDCl3, δ): 4.31 (2H, d, J=5.2 Hz), 5.24 (2H, s), 6.99 (1H, br, t, J=5.2 Hz), 7.38 (5H, s), 7.64 (1H, t, J=7.9 Hz), 8.15 (1H, d, t, J=7.9 Hz, 2.2 Hz), 8.35 (1H, d, t, J=7.9 Hz, 2.2 Hz), 8.64 (1H, t, J=2.2 Hz); APCI-MS (CHCl3) (m/z): 315 (M+ +1)

Provenance & Evidence