Hydroxyamine hydrochloride → methyl 3-chloro-2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-4-fluoro-5-[N-hydroxyethanimidoyl]benzoate
Reaction equation
[C:1]([C:4]1[C:5]([F:23])=[C:6]([Cl:22])[C:7]([N:14]2[CH2:19][C@H:18]([CH3:20])[O:17][C@H:16]([CH3:21])[CH2:15]2)=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=O)[CH3:2].Cl.[NH2:25][OH:26]>CO.N1C=CC=CC=1>[Cl:22][C:6]1[C:7]([N:14]2[CH2:19][C@H:18]([CH3:20])[O:17][C@H:16]([CH3:21])[CH2:15]2)=[C:8]([CH:13]=[C:4]([C:1](=[N:25][OH:26])[CH3:2])[C:5]=1[F:23])[C:9]([O:11][CH3:12])=[O:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methyl 5-acetyl-3-chloro-2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-4-fluorobenzoate (Intermediate 107, 800 mg, 2.32 mmol) in methanol:Pyridine (1:1, 6 mL) was added hydroxylamine hydrochloride (223 mg, 3.48 mmol) and the mixture was stirred at room temperature for 12 hours. Solvents were removed under vacuum and the residue was subjected to silica gel column chromatography using a gradient of ethyl aacetate in pet. ether to give title compound. Yield: 700 mg (87%).