[C:1]([CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([O:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5]1)#[N:2].C[Si]([N:23]=[N+:24]=[N-:25])(C)C.C([Sn](=O)CCCC)CCC.C1(C)C=CC=CC=1>CO>[N:2]1[NH:23][N:24]=[N:25][C:1]=1[CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([O:10][C:11](=[O:18])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:6][CH2:5]1
A mixture of trans-benzoic acid 4-cyanomethyl-cyclohexyl ester (3.42 g) obtained in Example (44a), trimethylsilyl azide (3.7 mL), di-n-butyltin oxide (348 mg), and toluene (30 mL) was heated at 110° C. for 48 hours. The progress of the reaction was stopped using methanol, and the reaction mixture was concentrated. The residue was diluted with ethyl acetate, followed by extraction with a saturated aqueous solution of sodium bicarbonate. The aqueous layer was acidified (pH=2) by the addition of 1 N hydrochloric acid, followed by extraction with ethyl acetate (×2). The organic layer was washed with saturated brine, then dried over sodium sulfate, and then concentrated to obtain the title compound (2.57 g, 64%) as a white solid.
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