Sodium Hydroxide → HCID 68680258, compound

HRID 2353906Notes

Reaction equation

HRID 2353906 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:13][CH2:12][CH2:11][C:10](=[N:14]O)[C:9]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:8]1=2)=[O:6])([CH3:3])[CH3:2].[BH4-].[Na+].[OH-].[Na+]>CO.CN(C=O)C>[CH:1]([O:4][C:5]([N:7]1[CH2:13][CH2:12][CH2:11][CH:10]([NH2:14])[C:9]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:8]1=2)=[O:6])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 86616068HCID 86616068, compound

Product 1

HCID 68680258HCID 68680258, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 8-chloro-5-hydroxyimino-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropyl ester (3.33 g, 11.2 mmole) and MoO3 (2.45 g, 17.0 μmmole) in MeOH (50.0 ml) was added a solution of sodium borohydride (2.13 g, 56.2 mmole) in DMF (50.0 ml). The reaction was stirred at room temperature overnight. To the reaction mixture was added 2.0N NaOH (aq) (100 ml). The precipitate was removed by filtration, and the filtrate was extracted with ethyl acetate (5×100 ml). The combined organics was washed with brine (3×500 ml). Dried over Na2SO4, filtered and concentrated to 100 ml, which was then treated with 4.0N HCl in dioxane (3.50 ml). Removal of solvents in vacuo gave a white solid, which washed with ethyl ether and dried under vacuum to provide the titled compound as hydrochloride salt (2.87 g, 80%). MS (ES+): 283 (M+H).

Workup

  1. customThe precipitate was removed by filtration
  2. extractionthe filtrate was extracted with ethyl acetate (5×100 ml)
  3. washThe combined organics was washed with brine (3×500 ml)
  4. dry with materialDried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to 100 ml, which
  7. additionwas then treated with 4.0N HCl in dioxane (3.50 ml)
  8. customRemoval of solvents in vacuo
  9. customgave a white solid, which
  10. washwashed with ethyl ether
  11. customdried under vacuum

Sources & evidence

ORD record
ord-76091eca0cc3467e9c3617266a9e15cb
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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