Diisopropylethylamine → 3-(aminomethyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

NMeArg(Tos)-Gly-OBzl (14.40 g, 29.4 mmol), Boc-D-Lys(Tfa) (10.00 g, 29.4 mmol), and HBTU (11.37 g, 62.0 mmol) were dissolved in methylene chloride (40 ml). After cooling to 0° C., DIEA (10.44 g, 62.0 mmol) was added and the reaction was allowed to proceed 20 minutes at 0° C. and 2 days at room temperature. The reaction mixture was diluted with ethyl acetate (800 ml), extracted with 200 ml portions of 0.2 N HCl (1×), sat. NaHCO3 (1×), and saturated NaCl (2×), dried (MgSO4), and evaporated under reduced pressure to a yellow solid. Purification by flash chromatography (silica gel; 5:1 EtOAc:acetonitrile) gave the title compound as a colorless solid (20.34 g, 85%). MP 78-85° C.; DCI-MS: [M+NH4 ]=831.

Provenance & Evidence