[C:1]([O:5][C:6]([O:8]N=C(C1C=CC=CC=1)C#N)=O)([CH3:4])([CH3:3])[CH3:2].Cl.[F:20][CH2:21][CH:22]([NH2:26])[CH2:23][CH:24]=[CH2:25].C(N(CC)CC)C.O>O1CCCC1>[F:20][CH2:21][CH:22]([NH:26][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:8])[CH2:23][CH:24]=[CH2:25]
Tert-Butyloxycarbonyloxyimino-2-phenylacetonitrile (3.35 g, 13.6 mmoles) in dry tetrahydrofuran (40 ml) is slowly added with ice cooling to a stirred mixture of 1-fluoro-2-amino-4-pentene hydrochloride (1.9 g, 13.6 mmoles) and triethylamine (2.78 g, 27.2 mmoles) in tetrahydrofuran (30 ml). After standing overnight at room temperature, water is added, the tetrahydrofuran is removed under reduced pressure, and the residue is extracted twice with ether. After washing with 1 N sodium hydroxide, then with water until neutral, the organic layer is dried and stripped to give 1-fluoro-2-tert-butoxycarbonylamino-4-pentene (2.33 g, 85%) as an oil which is used without further purification.
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