Dichloromethane → 1,4-Benzenedimethanamine

Participants

Reaction Steps

A solution of (S)-2-chloro-3-carboxy-5-(2-azetidinylmethoxy)pyridine 10 (R1=Cl and n=1) (2 mmol) and the linker molecule 1,4-bisaminomethylbenzene (1 mmol) in CH2Cl2 (5 mL) is prepared under argon in a flask equipped with magnetic stirrer and a drying tube. To this solution is added dicyclohexylcarbodiimide (solid, 2.2 mmol). The progress of the reaction is followed by tlc and after reaction occurs, the reaction solution is quenched in water, aqueous sodium bicarbonate is added and the aqueous mixture is extracted with methylene chloride. The organic layer is washed with aqueous Na2CO3 and with H2O, dried (Na2SO4), filtered and concentrated under reduced pressure to give the crude product. The desired compound 39 (where R1=Cl and n=1) is obtained by purification of the crude product with the use of HPLC.

Provenance & Evidence