Potassium Hydroxide → HCID 56979675, compound

HRID 2185778Notes

Reaction equation

HRID 2185778 reaction equation
Cl.[NH2:2][OH:3].[OH-].[K+].[F:6][C:7]([CH3:38])([CH3:37])[CH2:8][CH2:9][C@H:10]1[C:14](=[O:15])[O:13][C@H:12]([C@@H:16]([NH:24][C:25]([C:27]2[CH:36]=[N:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]=2)=[O:26])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:11]1>CO>[CH2:17]([CH:16]([NH:24][C:25]([C:27]1[CH:36]=[N:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1)=[O:26])[CH:12]([OH:13])[CH2:11][CH:10]([C:14](=[O:15])[NH:2][OH:3])[CH2:9][CH2:8][C:7]([F:6])([CH3:38])[CH3:37])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 57271532HCID 57271532, compound

Product 1

HCID 56979675HCID 56979675, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydroxylamine hydrochloride (1.55 g, 22.4 mmol) and KOH (1.51 g, 26.7 mmol) were combined in anhydrous methanol (20 mL) and stirred for 30 minutes under a dry nitrogen atmosphere, and then filtered. To the resulting filtrate was added the product from Method E (500 mg, 1.17 mmol) and the reaction mixture was stirred for 16 hours at room temperature. The solvent was removed in vacuo and the residue solvated in EtOAc (50 mL) and transferred to a separated funnel. The organic layer was washed with water and brine and dried (MgSO4). After filtration the solvent was removed in vacuo and the remaining residue recrystallized (methylene chloride/Hexanes) to give a pale yellow solid (330 mg, 58%) m.p. 165-166° C.

Workup

  1. filtrationfiltered
  2. stirringthe reaction mixture was stirred for 16 hours at room temperature
  3. customThe solvent was removed in vacuo
  4. customtransferred to a separated funnel
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationAfter filtration the solvent
  8. customwas removed in vacuo
  9. customthe remaining residue recrystallized (methylene chloride/Hexanes)

Sources & evidence

ORD record
ord-d17a2c5caca54c509c96def699f10add
Source dataset
uspto-grants-2002_06
Patent number
US06403587B1

Reaction notes

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