[CH2:1](Br)[C:2]#[CH:3].Cl.[CH3:6][O:7][C:8](=[O:23])[CH:9]([NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:10][NH2:11].C(N(CC)CC)C>C1COCC1>[CH3:6][O:7][C:8](=[O:23])[CH:9]([NH:12][C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[CH2:10][NH:11][CH2:3][C:2]#[CH:1]Propargyl bromide (1.6 mL, 14.4 mmol) is added to a solution of 3-amino-2-benzyloxycarbonylamino-propionic acid methyl ester hydrochloride (4.0 g, 13.9 mmol) and triethylamine (4.1 mL, 29.4 mmol) in THF (46 mL). The resulting mixture is heated to 50° C. and stirred overnight then cooled to RT and concentrated in vacuo. The crude residue is diluted with methylene chloride, washed with saturated NaHCO3 and brine then the organic layer is dried over MgSO4, filtered and concentrated in vacuo. The crude material (4.0 g) is taken on to the subsequent step without further purification. 1H NMR (CDCl3, 300 MHz) δ7.25-7.30 (m, 5H), 5.75 (bs, 1H), 5.20 (s, 2H), 4.45 (bs, 1H), 3.80 (s, 3H), 3.75 (m, 1H), 3.31 (s, 2H), 3.08 (dd, 1H), 2.98 (dd, 1H), 2.20 (t, 1H). EI MS, [M+H]+=291.
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