1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67423004, compound

Participants

Reaction Conditions

Reaction Steps

To N-Boc-4-(tributylstannyl)-L-phenylalanine (1.67 g, 3.00 mmol, 1.00 equiv) and L-phenylalanine methyl ester hydrochloride (647 mg, 3.00 mmol, 1.00 equiv) in CH2Cl2 (30 mL) at 0° C. was added EDCI (1.15 g, 6.00 mmol, 2.00 equiv), HOBt (810 mg, 6.00 mmol, 2.00 equiv), n,n-diisopropylethyl amine (1.56 mL, 9.00 mmol, 3.00 equiv) and 4-(Dimethylamino)pyridine (36 mg, 0.30 mmol, 0.10 equiv). After stirring for 1 hr at 0° C., the reaction mixture was allowed to stirred at room temperature for 12 hr. The reaction mixture was quenched with water (20 mL), and CH2Cl2 (10 mL) was added. The phases were separated and the aqueous phase was extracted with CH2Cl2 (2×10 mL). The combined organic phases were washed with brine (10 mL) and dried (Na2SO4). concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with hexane/EtOAc 3:1 (v/v) to afford 1.72 g of the title compound as a white foam (80% yield).

Provenance & Evidence