[CH3:1][O:2][C:3](=[O:14])[C:4]([Cl:13])([Cl:12])[CH2:5][NH:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.[Cl:15][C:16]1[N:21]=[C:20](Cl)[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][N:17]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]([Cl:12])([Cl:13])[CH2:5][N:6]([C:18]1[C:19]([N+:23]([O-:25])=[O:24])=[CH:20][N:21]=[C:16]([Cl:15])[N:17]=1)[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1A solution of 1.5 g (0.0063 mole) of 2,2-dichloro-3-cyclopentylamino-propionic acid methyl ester in 3 mL of ethyl acetate was added over 5 minutes to a cooled (0 degrees) mixture of 0.81 g (0.0042 mole) of 2,4-dichloro-5-nitro-pyrimidine, 1.76 g (0.02 mole) of sodium bicarbonate and 15 mL of ethyl acetate. The cooling bath was removed and the mixture stirred for 24 hours at room temperature and then 24 hours at 75 degrees. Activated charcoal was added and after stirring briefly, the mixture was filtered through a pad of Celite, washing the filter pad with ethyl acetate. The filtrate was concentrated under reduced pressure to give 2.4 g of 3-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-2,2-dichloro-propanoic acid methyl ester (IV-298) as a yellow thick oil. This material was used directly in the next step without further purification.
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