Hydroxyamine hydrochloride → methyl 3-chloro-2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-4-fluoro-5-[N-hydroxyethanimidoyl]benzoate

HRID 577905Notes

Reaction equation

HRID 577905 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

HCID 443297Hydroxyamine hydrochlorideHCID 86658064methyl 5-acetyl-3-chloro-2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-4-fluorobenzoate2×

Product 1

HCID 86658094methyl 3-chloro-2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-4-fluoro-5-[N-hydroxyethanimidoyl]benzoate

Reagents, catalysts & solvents 1

HCID 22021344Pyridine methanolSolvent

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%).

Workup

  1. customSolvents were removed under vacuum

Sources & evidence

ORD record
ord-2e75eda3a01d4641bebdcc7967125d5d
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

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