[CH:1]1([CH2:4][O:5][C@H:6]2[C@H:10]([NH:11][C:12]3[C:13](=[O:25])[N:14]([CH2:19][C:20]([O:22]CC)=[O:21])[C:15]([Cl:18])=[CH:16][N:17]=3)[CH2:9][O:8][CH2:7]2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl>CCO>[CH:1]1([CH2:4][O:5][C@H:6]2[C@H:10]([NH:11][C:12]3[C:13](=[O:25])[N:14]([CH2:19][C:20]([OH:22])=[O:21])[C:15]([Cl:18])=[CH:16][N:17]=3)[CH2:9][O:8][CH2:7]2)[CH2:3][CH2:2]1To a stirred solution of 3-(trans-3-cyclopropylmethoxytetrahydrofuran-4-ylamino)-6-chloro-1-ethoxycarbonylmethylpyrazinone from step 6 above (0.5 g, 1.3 mmol) and aqueous NaOH (0.65 mL of a 4.0 N solution, 2.6 mmol) in EtOH (7 mL) was stirred at ambient temperature for 18 h. Aqueous HCl (0.43 mL of a 6.0 N solution, 2.6 mmol) was added and the solvents were removed in vacuo. The residue was partitioned between CH2Cl2 and water. The organic phase was separated, dried over MgSO4, filtered and the solvent was removed in vacuo to give the title compound as an amorphous solid (0.4 g; HPLC RT=5.88 min, method A).
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