Ammonium Chloride → HCID 11688077, compound

HRID 1790654Notes

Reaction equation

HRID 1790654 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([O:12][C:13]([N:15]1[C@H:22]([CH3:23])[CH2:21][CH2:20][C@H:19]2[C@H:17]([O:18]2)[CH2:16]1)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl-].[NH4+]>CO.O>[CH2:5]([O:12][C:13]([N:15]1[CH2:16][C@@H:17]([OH:18])[C@H:19]([N:1]=[N+:2]=[N-:3])[CH2:20][CH2:21][C@H:22]1[CH3:23])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 11557975HCID 11557975, compound

Product 1

HCID 11688077HCID 11688077, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium azide (1.8 g, 27.7 mmol) was added to a (1R,4R,7S)-4-Methyl-8-oxa-3-aza-bicyclo[5.1.0]octane-3-carboxylic acid benzyl ester (2.4 g, 9.2 mmol, Example 1e) and ammonium chloride (1.48 g, 27.7 mmol) in MeOH (16 ml) and H2O (1.6 ml), then was refluxed overnight. The reaction mixture was concentrated in vacuo by rotary evaporation, then was diluted with water (5 ml) and extracted with EtOAc (10 ml). The organic layer was then extracted with water, brine, dried with MgSO4, filtered, concentrated in vacuo by rotary evaporation, and chromatographed (silica gel, 25% EtOAc/hexanes) to yield the title compound (1.76 g, 63%); Liquid chromatgraphy/Electrospray mass spec: M+H+=305.2.

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe reaction mixture was concentrated in vacuo by rotary evaporation
  3. additionwas diluted with water (5 ml)
  4. extractionextracted with EtOAc (10 ml)
  5. extractionThe organic layer was then extracted with water, brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo by rotary evaporation
  9. customchromatographed (silica gel, 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-84699b9770274b688649385a7f1ece24
Source dataset
uspto-grants-2006_07
Patent number
US07071184B2

Reaction notes

Loading…