Hydrochloric Acid → HCID 53803346, compound

HRID 2270562Notes

Reaction equation

HRID 2270562 reaction equation
[C:1]([O:5][C:6]([N:8](C(OC(C)(C)C)=O)[CH2:9][C:10]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:11]=1[N:19]1[CH:23]=[CH:22][CH:21]=[N:20]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].Cl.C(=O)([O-])O.[Na+]>O.O.O.O.O.O.[Ni](Cl)Cl.CO>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[CH:15]=[C:14]([NH2:16])[CH:13]=[CH:12][C:11]=1[N:19]1[CH:23]=[CH:22][CH:21]=[N:20]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 53850736HCID 53850736, compound

Product 1

HCID 53803346HCID 53803346, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

To a mixture of the compound (4.15 g) obtained in Example 500a, nickel (II) chloride hexahydrate (0.183 g) and methanol (300 ml), sodium borohydride (2.43 g) was added. The reaction mixture was stirred at room temperature for 55 min; thereafter, 2 N HCl was added to render the reaction solution acidic and then a saturated aqueous sodium hydrogencarbonate solution was added to render the reaction solution basic; subsequently, the reaction mixture was concentrated under reduced pressure. To the resulting residue, water was added and the resulting mixture was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was recrystallized from ethyl acetate/n-hexane to give the titled compound (yield, 89%).

Workup

  1. additionwas added
  2. concentrationsubsequently, the reaction mixture was concentrated under reduced pressure
  3. additionTo the resulting residue, water was added
  4. extractionthe resulting mixture was subjected to extraction with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried with anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-81436030a18946728d1dccd1b3949c9b
Source dataset
uspto-grants-2001_12
Patent number
US06331553B1

Reaction notes

Loading…