Hydrochloric Acid → HCID 178456094, compound

HRID 1892815Notes

Reaction equation

HRID 1892815 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:15]#[N:16])[CH2:13][CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:17]=[N+:18]=[N-:19].[Na+].Cl>[Br-].[Zn+2].[Br-].C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:15]1[NH:19][N:18]=[N:17][N:16]=1)[CH2:13][CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 66935237HCID 66935237, compound

Product 1

HCID 178456094HCID 178456094, compoundYield 58.9%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To N-benzyloxycarbonyl-(1R)-1-cyanopropylamine (85.6 mg) in suspension (3 ml), sodium azide (28 mg) and zinc bromide (88.3 mg) were added and the mixture was stirred under heating and reflux for 24 hours. 3N hydrochloric acid and ethyl acetate were added to the reaction solution and the mixture was stirred until there were no longer any insolubles. The obtained solution was extracted with ethyl acetate, then the organic layer was concentrated. 0.25N sodium hydroxide aqueous solution was added to the residue, the mixture was stirred for 30 minutes, and the insoluble compound was filtered. 6N hydrochloric acid was added to the filtrate to adjust to pH 1, then this was concentrated. The residue was diluted with 1N hydrochloric acid, then the solids were collected by filtration to obtain the title compound (60.4 mg).

Workup

  1. temperatureunder heating
  2. temperaturereflux for 24 hours
  3. stirringthe mixture was stirred until there
  4. extractionThe obtained solution was extracted with ethyl acetate
  5. concentrationthe organic layer was concentrated
  6. addition0.25N sodium hydroxide aqueous solution was added to the residue
  7. stirringthe mixture was stirred for 30 minutes
  8. filtrationthe insoluble compound was filtered
  9. addition6N hydrochloric acid was added to the filtrate
  10. concentrationthis was concentrated
  11. additionThe residue was diluted with 1N hydrochloric acid
  12. filtrationthe solids were collected by filtration

Sources & evidence

ORD record
ord-71a9bdf5c099404691770ad39f30b27f
Source dataset
uspto-grants-2013_08
Patent number
US08507714B2

Reaction notes

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