Trityl chloride → 2-(2-Hydroxyethyl)3-oxo-1,7-bis(triphenylmethyl)-1,4,7-triazaheptane

Participants

Reaction Steps

6-Amino-2-(2-hydroxyethyl)-3-oxo-1-(triphenylmethyl)-1,4-diazahexane (15.0 g, 37.2 mmol) (Example 9 (a)) was dissolved in 150 ml DMF and triphenylmethyl chloride (10.35 g, 37.2 mmol) and methylmorpholine (3.75 g, 37.2 mmol) was added. After being stirred for 24 hours at ambient temperature, the reaction mixture was filtered and poured into 200 ml of ice water. After 1 hour stirring, filtration and thoroughly washing the precipitate with water, the solid was dried in vacuo at 50° C. to yield 22 g of crude product. The product was dissolved in chloroform/toluene/methanol (80/16/14) and purified on silica to yield 6.6 g (27%) of 2-(2-hydroxyethyl)3-oxo-1,7-bis(triphenylmethyl)-1,4,7-triazaheptane as white crystals, m.p. 71°-72° C., FAB MS: 646(M+1). The structure was confirmed by 13C NMR.

Provenance & Evidence