[H-].[Na+].[C:3]1([CH2:9][O:10][C:11]([NH:13][C:14]2([C:17]([O:19][CH3:20])=[O:18])[CH2:16][CH2:15]2)=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.I[CH3:22]>CN(C=O)C.O>[CH3:22][N:13]([C:11]([O:10][CH2:9][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)=[O:12])[C:14]1([C:17]([O:19][CH3:20])=[O:18])[CH2:16][CH2:15]1Sodium hydride (995 mg, 41.466 mmol) was taken up in DMF (50 mL) and was cooled to 0° C. for 30 min. Then a mixture of methyl 1-({[(phenylmethyl)oxy]carbonyl}amino)cyclopropanecarboxylate (6.46 g, 25.916 mmol) in DMF (25 mL) was slowly added over 10 min. The resulting mixture was allowed to stir for 45 min, and then iodomethane (4.84 mL, 77.74 mmol) was added, and the reaction was allowed to warm to room temperature overnight. The mixture was then carefully diluted with water (10 mL), and the aqueous layer was extracted with Et2O (5×50 mL). The organic extracts were washed with water (5×50 mL), then dried over Na2SO4 and concentrated in vacuo. The crude residue was purified via Combiflash, utilizing a 0%-50 EtOAc/Hex gradient to provide methyl 1-(methyl{[(phenylmethyl)oxy]carbonyl}amino)cyclopropanecarboxylate (16.9 g, >100%) LCMS: (M+H)+: 264.1.
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