Cl.[CH2:2]([O:4][C:5](=[O:9])[CH2:6][NH:7][CH3:8])[CH3:3].[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]#[C:18][C:19]([OH:21])=O.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]#[C:18][C:19]([N:7]([CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:9])[CH3:8])=[O:21]To a solution of sarcosine ethyl ester hydrochloride (1.14 g, 7.44 mmol) and 3-(2-fluorophenyl)prop-2-ynoic acid (1.22 g, 7.44 mmol) in anhyd. CH2Cl2 was added NMM (10 mL, 8.93 mmol), followed by EDCI.HCl (1.86 g, 9.67 mmol) and DMAP (0.99 g, 8.2 mmol). The reaction mixture was stirred for 5 h at room temperature and diluted with CH2Cl2. The resulting solution was washed with a 0.5N HCl solution (2×25 mL), a 0.5N NaOH solution (2×25 mL) and a saturated NaCl solution. The organic layer was dried (MgSO4), concentrated onto silica gel under reduced pressure and purified by flash chromatography (30% EtOAc/hex) to yield ethyl 2-[3-(2-fluorophenyl)-N-methylprop-2-ynoylamino]acetate (1.50 g, 77%) as a yellow oil: TLC (50% EtOAc/hex) Rf 0.54; HPLC ES-MS m/z (rel abundance) 264 (100%).
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