N,N-Diethylethylenediamine → HCID 19989825, compound

Participants

Reaction Steps

1.71 g of (±) 2,3-dihydro-3-(4-methoxyphenyl)-4-oxo-1,5-benzothiazepin-5-(4H)-acetic acid of Step B of Example 14, 17 ml of methylene chloride, 1.74 g of N,N-diethylethylene diamine and 3.82 g of 1-ethyl-3-(dimethylaminopropyl)-carbodiimide hydrochloride were stirred for 90 minutes and the solution was poured over 50 ml of water. 10 ml of a saturated aqueous solution of sodium bicarbonate were added, and extraction was done with methylene chloride. The extracts were washed with water, dried and the solvent was eliminated under reduced pressure to obtain 3.6 g of crude product which was chromatographed on silica (eluant: methylene chloride-methanol 8-2) to obtain 1.6 g of the expected product in the form of a base. The base was dissolved in 5 ml of isopropanol and a solution of hydrochloric acid in ethyl acetate was added to obtain 1.5 g of the expected hydrochloride which was crystallized from isopropanol to obtain 525 mg of pure product melting at 160° C.

Provenance & Evidence