[Br:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][O:7][CH:8]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.Cl.[NH2:19][CH2:20][C:21]#[N:22].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][CH:8]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:9]([NH:22][CH2:21][C:20]#[N:19])=[O:11])=[CH:16][CH:17]=1To a solution of 2-[(4-bromobenzyl)oxy]4-methylpentanoic acid in DMF (15 mL) was added aminoacetonitrile hydrochloride (1.9 g, 20.6 mmoles) and HATU (5 g, 13.3 mmoles). After stirring for one minute, triethylamine (5.3 mL, 38.3 mmoles) was added in one portion. The reaction was stirred overnight, diluted with ethyl acetate and water. The organic phase was separated and washed twice with 1.2 N hydrochloric acid, brine and dried over magnesium sulfate. After concentration under reduced pressure, 2-[(4-bromobenzyl)oxy]-N-(cyanomethyl)-4-methylpentanamide was obtained.
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