Hydrochloric Acid → HCID 53692438, compound

HRID 2270560Notes

Reaction equation

HRID 2270560 reaction equation
[C:1]([O:5][C:6]([N:8]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[C:11]=1[O:19][CH2:20][CH3:21])=[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:25]([O:24][C:22]([N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[C:11]=1[O:19][CH2:20][CH3:21])=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 54256258HCID 54256258, compound

Product 1

HCID 53692438HCID 53692438, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

To a mixture of the compound (5.09 g) obtained in Example 417d, nickel (II) chloride hexahydrate (61 mg) and methanol (130 ml), sodium borohydride (1.46 g) was added. The reaction mixture was stirred at room temperature for 20 min and, after addition of 2 N HCl, adjusted to pH 8 with a saturated aqueous sodium hydrogencarbonate solution and then concentrated under reduced pressure. To the resulting residue, water was added and the 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 purified by silica gel column chromatography (eluent, ethyl acetate:n-hexane=1:4) to give the titled compound (yield, 85%).

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. additionTo the resulting residue, water was added
  4. extractionthe 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 purified by silica gel column chromatography (eluent, ethyl acetate:n-hexane=1:4)

Sources & evidence

ORD record
ord-7ee9e804d5354d07ab7fefdf92fd74cd
Source dataset
uspto-grants-2001_12
Patent number
US06331553B1

Reaction notes

Loading…