Hydrochloric Acid → HCID 178454247, compound

HRID 1169385Notes

Reaction equation

HRID 1169385 reaction equation
[N+:1]([C:4]1[CH:28]=[CH:27][C:7]([CH2:8][NH:9][C:10]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[N:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:6][CH:5]=1)([O-])=O.[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>C1COCC1.CO.[Ni](Br)Br>[C:15]([O:14][C:12]([N:11]=[C:10]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[NH:9][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:28][CH:27]=1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 178454248HCID 178454248, compound

Product 1

HCID 178454247HCID 178454247, compoundYield 66.5%

Reagents, catalysts & solvents 3

HCID 278492Nickel(II) bromideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To N-(4-nitrobenzyl)-N′,N″-bis(tert-butoxycarbonyl)guanidine (1.97 g, 4.99 mmol) dissolved in a mixed solvent of THF (25 ml) and methanol (25 ml) were added at 0° C. nickel bromide (109 mg, 0.50 mmol) and sodium borohydride (757 mg, 20.0 mmol) in the order, and the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was mixed with 1 N hydrochloric acid (40 ml) at 0° C., and the resulting mixture was stirred at the same temperature for 5 minutes. The resulting mixture was adjusted to about pH 8 by adding an aqueous saturated solution of sodium bicarbonate and was extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate and was then concentrated under reduced pressure, diisopropyl ether was added to the residue, and an insoluble material was collected by filtration. The insoluble material was washed with diisopropyl ether and was then dried under reduced pressure to obtain 4-[N′,N″-bis(tert-butoxycarbonyl)guanidinomethyl]aniline (1.21 g, 3.32 mmol, 66%).

Workup

  1. stirringthe resulting mixture was stirred at the same temperature for 5 minutes
  2. extractionwas extracted with ethyl acetate
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. concentrationwas then concentrated under reduced pressure, diisopropyl ether
  5. additionwas added to the residue
  6. filtrationan insoluble material was collected by filtration
  7. washThe insoluble material was washed with diisopropyl ether
  8. customwas then dried under reduced pressure

Sources & evidence

ORD record
ord-5096ac48ddbe432a960cc73e77c69afd
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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