Diisopropylcarbodiimide → HCID 68352357, compound

Participants

Reaction Steps

A solution of 119 mg (0.5 mmol) theophylline-7-acetic acid in 5 ml DMF was dropped for 15-20 minutes into pre-heated at 60° C. solution of 80 μl N,N′-diisopropyl carbodiimide (DIC) in 2.5 ml DMF. The mixture was subsequently heated for 4 hours at the same temperature. After cooling the solvent was evaporated in a vacuum. The residue was dissolved in minimal amount of chloroform and purified by flash chromatography on Silicagel-60A with chloroform:methanol (98:2) as eluent. The fractions with the desired product were pooled and evaporated, yielding 82 mg (44%) from the compound Th69 as a white powder. Rf=0.68 (chloroform/methanol (9/1), Rf=0.23 (ethyl acetate). The empirical formula (F.W. 365) was confirmed by the results from LC/MS. The main molecular peak was found at 365 with a second peak at 387 for the sodium salt. The m.p. of the product was 117-120° C. The 1H-NMR Spectrum (300 MHz) was consistent with the expected structure.

Provenance & Evidence