Dicyclohexylcarbodiimide → HCID 131716194, compound

Participants

Reaction Steps

Stir 3.15 g (13.6 mmoles) of Boc-Ile, 2.08 g (13.6 mmoles) of 1-HOBT, and 1.34 g (12.3 mmoles) of 2-(aminomethyl)pyridine in 150 ml of CH2Cl2 for 10 minutes. Add 2.81 g (13.6 mmoles) of DCC and stir at room temperature for 35 minutes, then filter off DCU. Extract the filtrate with aq. NaHCO3, filter the organic layers through Na2SO4, and concentrate. Filter off DCU again, then chromatograph the crude production silica gel, eluting with 4% MeOH-CH2Cl2, to obtain 3.94 g (100%) of product. The product, Boc-Ile-AMP, is crystallized from EtOAc-hexane to give a first crop of 2.28 g with a m.p. of 102°-103.5°. Second and third crops totalling 1.50 g are also collected. Calc. for C17H27N3O3 : C, 63.52; H, 8.47; N, 13.07. Found: C, 63.37; H, 8.55; N, 12.86.

Provenance & Evidence