[CH:1]([C:4]1[NH:8][C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:5]=1)([CH3:3])[CH3:2].[H-].[Na+].[NH2:21]Cl.O>CN(C=O)C.CCOCC>[NH2:21][N:8]1[C:4]([CH:1]([CH3:2])[CH3:3])=[CH:5][C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:7]1[C:9]([O:11][CH2:12][CH3:13])=[O:10]To a solution of 1B (2.53 g, 10 mmol) in dry DMF (40 ml) was added NaH (60%, 550 mg, 13.75 mmol) in one portion. After H2 evolution subsided, NH2Cl in ether (85 ml) was added dropwise via additional funnel. The reaction mixture was stirred at room temperature for 1 h. Water was added, the mixture was extracted with ether (×3), the combined ether layers were washed with brine, dried over MgSO4, concentrated in vacuo to give 1C (2.50 g, 93%) as an oil. Compound 1C had an analytical HPLC retention time=2.893 min. (Chromolith SpeedROD column 4.6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 ml/min, monitoring at 220 nm) and a LC/MS M++1=269+.
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