Trifluoroacetic acid → HCID 131734453, compound

Participants

Reaction Steps

N-tert-butoxycarbonyl O-propynyl L-seryl glycine methyl ester (2.52 g, 8.02 mmol) was dissolved in CH2Cl2 (15 mL). Trifluoroacetic acid (15 mL) was added and the reaction mixture stirred for 2 h at room temperature. The solvent and bulk of excess TFA were removed and the residue washed with Et2O (2×15 mL). The diethyl ether was decanted off and the residue dried under vacuum before being redissolved in CH2Cl2 (70 mL). The solvent was evaporated and the residue dried under high vacuum overnight affording a brown, viscous oil (2.32 g, 88%); δH (200 MHz; d6-DMSO) 8.97 (1H, t, J 6, NH), 8.31 (3H, br s, NH3+), 4.21 (2H, d, J 2, CH2CCH), 4.16-4.05 (1H, m, CαH(propSer)), 3.96 (2H, d, J 6, CαH2(Gly)), 3.83 (1H, dd, J 11 and 4, CHH), 3.74 (1H, dd, J 11 and 6, CHH), 3.65 (3H, s, OCH3), 3.55 (1H, t, J 2, CCH).

Provenance & Evidence