N.CC1C=CC(S([N:12]2[CH2:20][CH2:19][O:18][C:17]3[CH:21]=[CH:22][C:23]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][C:16]=3[O:15][CH2:14][CH2:13]2)(=O)=O)=CC=1.[Na].[Cl-:31].[NH4+]>C(OCC)(=O)C.CO>[ClH:31].[O:18]1[C:17]2[CH:21]=[CH:22][C:23]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][C:16]=2[O:15][CH2:14][CH2:13][NH:12][CH2:20][CH2:19]1
To ammonia (50 mL) and CH3OH (9 mL) at -78° C. add 4-[(4-methylphenyl)sulfonyl]-9-[(methylsulfonyl)amino]-3,4,5,6-tetrahydro-2H-1,7,4-benzodioxazonine (8.5 g, 20 mmol) and sodium spheres (4.5 g, 0.20 mol). Monitor the progress of the reaction by thin-layer chromatography. Upon completion add ammonium chloride (11 g) and allow the reaction to warm to room temperature. Slurry the residue in ethyl acetate and remove the solid material by suction filtration through celite. Remove the solvent in vacuo. Dissolve the residue in CH3OH and add methanolic hydrochloric acid. Remove the solvent in vacuo and recrystallize from acetonitrile to obtain the title compound.
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