Dimethylformamide → HCID 131730293, compound

Participants

Reaction Steps

Fmoc-β-alanine (84.5 g, 271 mmol) and N-hydroxysuccinimide (31.2 g, 271 mmol) are dissolved in dichloromethane (850 mL) and DMF (43 mL) with magnetic stirring. N,N-dicyclohexylcarbodiimide (56.0 g, 271 mmol) dissolved in dichloromethane (100 mL) is added in one portion. After stirring 1.5 hours at room temperature, the reaction mixture was filtered, and transferred to a mixture of serinol (24.7 g, 271 mmol) in pyridine (380 mL) and allowed to react 16 hours overnight. The mixture is evaporated to a semi-solid residue, and co-evaporated 3×400 mL toluene to remove the remaining pyridine. The solid residue is refluxed in dichloromethane (3.0 L) and stored at −20° C. for 2 hours. The product was collect by filtration in a sintered glass funnel, and washed 2×1000 mL dichloromethane, and 1×1000 mL diethyl ether. Drying overnight under high vacuum yielded 92.8 g (89%) of 1.

Provenance & Evidence