Hydroxyamine hydrochloride → HCID 86613802, compound

HRID 2378124Notes

Reaction equation

HRID 2378124 reaction equation
[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[N:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=2)[C@H:10]([N:21]([CH2:28][C:29]2[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=2)[C:22](=[O:27])[CH2:23][C:24](=O)[CH3:25])[CH2:9][C@@H:8]1[CH2:43][CH3:44])=[O:6])([CH3:3])[CH3:2].Cl.[NH2:46]O.C([O-])(=O)C.[Na+]>CO>[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[N:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=2)[C@H:10]([N:21]([CH2:28][C:29]2[CH:34]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:32]=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=2)[C:22]2[O:27][N:46]=[C:24]([CH3:25])[CH:23]=2)[CH2:9][C@@H:8]1[CH2:43][CH3:44])=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86613801HCID 86613801, compound

Product 1

HCID 86613802HCID 86613802, compoundYield 5.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (+/−)-cis-4-[(3,5-bis-trifluoromethyl-benzyl)-(3-oxo-butyryl)-amino]-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid isopropyl ester (225 mg, 0.35 mmol) in MeOH (1.7 mL) at 0° C., add hydroxylamine hydrochloride (37 mg, 0.53 mmol) and sodium acetate (1.4 mg, 0.017 mmol). Stir the reaction mixture under reflux overnight. Cool the mixture and remove the solvents under reduced pressure. Dilute the residue with ethyl acetate and brine. Separate the layers, and dry the organic phase over magnesium sulfate, filter, and concentrate in vacuo. Purify the residue by flash chromatography, eluting with hexanes/ethyl acetate, to afford the title compound (12 mg, 5%). MS (ES+): 639 (M+H).

Workup

  1. temperatureunder reflux overnight
  2. temperatureCool the mixture
  3. customremove the solvents under reduced pressure
  4. additionDilute the residue with ethyl acetate and brine
  5. customSeparate the layers
  6. dry with materialdry the organic phase over magnesium sulfate
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customPurify the residue by flash chromatography
  10. washeluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-423de47333c94a20a397ca68a20a2fcc
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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