Triethylamine → HCID 18429271, compound

Participants

Reaction Conditions

Reaction Steps

5-[N-(2,3-Diacetoxypropionyl)amino]-3-acetoxymethyl-2,4,6-triiodobenzoyl chloride (7.71 g, 9.9 mmol), 2,3-dihydroxypropylamine (1.48 g, 16.2 mmol), lithium bromide (90 mg, 1 mmol) and triethylamine (2.27 ml, 16.2 mmol) were mixed in tetrahydro-furan (55 ml) at ambient temperature. The temperature was increased to 65° C. and held there for 26 h with efficient stirring, and the mixture was then evaporated to dryness. The residue was dissolved in a mixture of water and methanol (6:1, 70 ml) and treated with a strongly basic anion exchange resin (Dowex 1×8) for 2.5 h. The resin was filtered off, the solution diluted with further water (50 ml) and treated with a strongly acidic cation exchange resin (Amberlyst 15) to bring the pH of the solution to 5.5-6.0. The resin was filtered off and the solution was treated with activated charcoal (0.35 g), filtered and evaporated to a light yellow to white solid residue. This was triturated with acetonitrile (20 ml) for 12 h, giving 5.8 g (70%) of a white crystalline residue.

Provenance & Evidence