Hydrochloric Acid → HCID 53803346, compound

HRID 2227475Notes

Reaction equation

HRID 2227475 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([N:10](C(OC(C)(C)C)=O)[CH2:11][C:12]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:13]=1[N:21]1[CH:25]=[CH:24][CH:23]=[N:22]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl.C(=O)([O-])O.[Na+]>O.O.O.O.O.O.[Ni](Cl)Cl.CO>[C:3]([O:7][C:8](=[O:9])[NH:10][CH2:11][C:12]1[CH:17]=[C:16]([NH2:18])[CH:15]=[CH:14][C:13]=1[N:21]1[CH:25]=[CH:24][CH:23]=[N:22]1)([CH3:6])([CH3:4])[CH3:5]

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

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

Workup

  1. concentrationconcentrated at reduced pressure
  2. additionWater was added to the resulting residue and extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated at reduced pressure
  6. customThe resulting residue was recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-18a69a5c7e1d497c8dbebe5bdf0bbd77
Source dataset
uspto-grants-2002_07
Patent number
US06414005B1

Reaction notes

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