Application of 6622-91-9 ,Some common heterocyclic compound, 6622-91-9, molecular formula is C7H8ClNO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
Example 12 Synthesis of N-[(4-pyridyl)acetyl]-D,L-alanine iso-butyl ester Following General Procedure F and using 4-pyridylacetic acid hydrochloride (Aldrich) and (D,L)-alanine iso-butyl ester hydrochloride (from Example B above), the title compound was prepared as a solid having a melting point of 64-66C. The reaction was monitored by tlc on silica gel (Rf = 0.43 10% methanol/dichloromethane) and purification was by silica gel chromatography. NMR data was as follows: 1H-nmr (CDCl3): delta = 8.51 (dd, J = 1.6, 2.8, 1.6, 2H); 7.23 (dd, J = 4.3, 1.6, 4.4, 2H); 6.71 (d, J = 6.8, 1H); 4.56 (quint., J = 7.3, 7.2, 1H); 3.88 (m, 2H); 3.53 (s, 2H); 1.89 (m, 1H); 1.36 (d, J = 7.2, 3H); 0.88 (d, J = 6.7, 6H). 13C-nmr (CDCl3): delta = 173.5, 169.3, 150.5, 144.4, 125.1, 72.1, 48.9, 43.0, 28.2, 19.5, 19.5, 18.9. C14H20N2O3 (MW = 264, Mass Spectroscopy (MH+ 265)) GENERAL PROCEDURE ELow Temperature BOP Coupling of Acid and Alcohol A solution of methylene chloride containing the carboxylic acid (100M%) and N-methyl morpholine (150 M%) was cooled to -20C under nitrogen. BOP (105 M%) was added in one portion and the reaction mixture was maintained at -20C for 15 minutes. The corresponding alcohol (120 M%) was added and the reaction mixture was allowed to warm to room temperature and stirred for 12 hours. The reaction mixture was then poured into water and extracted with ethyl acetate (3x). The combined ethyl acetate portions were backwashed with saturated aqueous citric acid (2x), saturated aqueous sodium bicarbonate (2x), brine (1x), dried over anhydrous magnesium sulfate or sodium sulfate and the solvent removed under reduced pressure to yield the crude product
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 6622-91-9, 2-(Pyridin-4-yl)acetic acid hydrochloride, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; Elan Pharmaceuticals, Inc.; ELI LILLY AND COMPANY; EP951464; (2005); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem