C[Si](C)(C)[O:3][CH2:4][CH2:5][O:6][C:7]1([C:11]#[N:12])[CH2:10][CH2:9][CH2:8]1.[NH2:15][OH:16].[C:17]([C:24]([O:26][CH2:27][CH3:28])=[O:25])#[C:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CCO>[CH2:22]([O:21][C:19](=[O:20])[C:18]([O:16][NH:15][C:11]([C:7]1([O:6][CH2:5][CH2:4][OH:3])[CH2:10][CH2:9][CH2:8]1)=[NH:12])=[CH:17][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:23]A solution of 1-(2-trimethylsilanyloxyethoxy)cyclobutanecarbonitrile (3.5 g, 16.4 mmol) and 50% aqueous hydroxylamine (1.08 g, 16.4 mmol) in EtOH (16 mL) was stirred in an oil bath heated at 80° C. for 2.5 hrs and then cooled to room temperature. To a solution was added drop-wise diethyl acetylenedicarboxylate (2.93 g, 17.2 mmol) in an ice-bath and the mixture stirred at room temperature for 5 hrs. This mixture was concentrated in vacuo to obtain 6.16 g of a crude brownish oil containing intermediate 25: 1H NMR (500 MHz, CDCl3) δ: 1.19-1.38 (6 H, m) 1.72-1.86 (2 H, m) 2.06-2.24 (2 H, m) 2.29-2.49 (2 H, m) 3.26-3.38 (2 H, m) 3.65-3.76 (2H, m) 4.11-4.19(2 H, m) 4.24-4.38(2 H, m) 5.67(0.25 H, s) 5.85 (0.5 H, s). HRMS (M+H) calcd for C15H25N2O7 345.1662, found 345.1648.
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