[H-].[Na+].[Cl:3][C:4]1[CH:8]=[CH:7][NH:6][C:5]=1[C:9]([O:11][CH3:12])=[O:10].C1(P(O[NH2:28])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C=O)C>[NH2:28][N:6]1[CH:7]=[CH:8][C:4]([Cl:3])=[C:5]1[C:9]([O:11][CH3:12])=[O:10]To a suspension of sodium hydride (60 percent, 1.5 g, 37.5 mmol) in DMF (250 mL) was added methyl 3-chloro-1H-pyrrole-2-carboxylate (5.0 g, 31.3 mmol) at 0° C., and the mixture was stirred for 25 min, followed by the addition of O-(diphenylphosphoryl)hydroxylamine (10.0 g, 43.75 mmol). The reaction mixture was stirred at RT for 4 h and quenched by aq. Na2SO3 solution. After stirred for another 5 min, the mixture was extracted with EtOAc (3×300 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to give crude product as a brown oil, which was purified by chromatography purification on silica gel (PE:EA=4:1) to obtain the title compound (5.00 g, 91%) as a white solid. MS (ES+) C6H7ClN2O2 requires: 174, 176. found: 175, 177 [M+H]+.
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