Hydrochloric Acid → [(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]-4-amino-2-fluoro-benzoate

HRID 1529529Notes

Reaction equation

HRID 1529529 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:39])[CH:5]=[C:6]([Cl:38])[C:7]=1[CH2:8][C@H:9]([O:20][C:21](=[O:37])[C:22]1[CH:27]=[CH:26][C:25]([NH:28]C(OC(C)(C)C)=O)=[CH:24][C:23]=1[F:36])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1.Cl.O1CCOCC1>>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:39])[CH:5]=[C:6]([Cl:38])[C:7]=1[CH2:8][C@H:9]([O:20][C:21](=[O:37])[C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][C:23]=1[F:36])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86720691[(1S)-2-(3,5-dichloro-1-oxidopyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]-4-(tert-butoxycarbonylamino)-2-fluorobenzoate

Product 1

HCID 86720692[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]-4-amino-2-fluoro-benzoateYield 79%

Procedure

[(1S)-2-(3,5-dichloro-1-oxidopyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]-4-(tert-butoxycarbonylamino)-2-fluorobenzoate (0.690 g, 1.19 mmol) was stirred in a 4N HCl in 1,4-dioxane solution (14.8 mL, 5.94 mmol). The reaction was stirred at room temperature for 3 hours. The solvent was removed in vacuo. The residue was purified by silica gel chromatography eluting sequentially with iso-hexane and 10% methanol in ethyl acetate to afford the title compound as a beige solid (0.451 g, 79%).

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was purified by silica gel chromatography
  3. washeluting sequentially with iso-hexane and 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-7ac2012943d74578925c175b78f86238
Source dataset
uspto-grants-2015_07
Patent number
US09090606B2

Reaction notes

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