Hydrochloric Acid → HCID 131716231, compound

Participants

Reaction Conditions

Reaction Steps

Tetrapeptide H-Ser(Bzl)-Gly-Leu-Gly-OCH3 : HCl.H-Leu-Gly-OCH3 (12.2 g, 51.3 mmol) was dissolved in DMF (200 mL). DIEA (24 mL, 139.8 mmol) was added to the solution. This first solution was cooled to 0° C. A second solution of Boc-Ser-(Bzl)-Gly-OH (16.42 g, 46.6 mmol) and DPPA (14.1 g, 51.26 mmol) in DMF (122 mL) was added with stirring to the first solution. The mixture was stirred for 20 h while the temperature of the mixture gradually came to room temperature. Concentration of the reaction mixture under reduced pressure gave an oil. The oil was dissolved in EtOAc. The solution was washed with 1N HCl, 1N NaHCO3 and H2O, dried (Na2SO4 /MgSO4) and concentrated to dryness to give an oil. Trituration of the latter oil with Et2O-hexane yielded Boc-Ser(Bzl-Gly-Leu-Gly-OCH3 as a solid (23.82 g). The latter compound (28.82 g) was dissolved in 1N HCl in glacial acetic acid (100 mL). The mixture was stirred at room temperature for 1 h and then concentrated under reduced vacuum to give an oil. Trituration of the oil with Et2O afforded the tetrapeptide as a solid (19.71 g, HCl salt).

Provenance & Evidence