Hydrochloric Acid → HCID 15462778, compound

Participants

Reaction Steps

2-Benzhydrylideneamino-3-pyridin-4-yl-2-pyridin-4-ylmethyl-propionic acid methyl ester (49.6 g, 113 mmol) was dissolved in anhydrous THF (640 ml). To the reaction was added 227 ml of a solution of 2.0 M aqueous hydrochloric acid (HCl). The mixture was stirred at ambient temperature for one hour. The reaction was subsequently concentrated under vacuum to remove the THF. The reaction was then partitioned between ethyl ether and water. The aqueous layer was washed two more times with ethyl ether. The pH of the aqueous layer was then adjusted to 9 with sodium carbonate (Na2CO3) and the solution is extracted with methylene chloride until virtually no product is left in the methylene chloride (CH2Cl2) layer. The CH2Cl2 extracts were combined, dried over Na2SO4, filtered and concentrated under vacuum to give 25.6 g (94.4 mmol) of the titled compound as a yellow solid.

Provenance & Evidence