Methanol → HCID 131730294, compound

Participants

Reaction Steps

N-Fmoc-β-Ala-Serinol (1, 93 g, 242 mmol) is co-evaporated 2×400 mL anh. pyridine, and then dissolved in 300 mL of the same solvent with magnetic stirring. The mixture is cooled in a ice bath, and DMT-Cl (86.1 g, 254 mmol) in 465 mL pyridine is added dropwise over a period of 1.5 hours. The ice bath is removed and the mixture is allowed to react for another hour at room temperature. Methanol (100 mL) is added and stirred for 15 min. to quench the remaining DMT-Cl. After evaporation in vacuo, the residue co-evaporated 3×400 mL with toluene. Silica gel column purification using ethyl acetate/methanol/triethylamine (95:5:0.25) as mobile phase yielded 90.6 g (55%) grams of isolated product 2.

Provenance & Evidence