Ammonium Chloride → HCID 86618889, compound

HRID 252421Notes

Reaction equation

HRID 252421 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][CH:16]([CH:30]([CH3:32])[CH3:31])[CH2:17][CH:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]3[CH2:21][O:20]3)[CH:13]=2)[N:8]([CH3:33])[CH:7]=1.[N-:34]=[N+:35]=[N-:36].[Na+].[Cl-].[NH4+]>CO>[N:34]([CH2:21][CH:19]([CH:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:17][CH:16]([CH2:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:33])[CH:7]=[C:6]2[CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH:30]([CH3:32])[CH3:31])[OH:20])=[N+:35]=[N-:36]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 86618879HCID 86618879, compound

Product 1

HCID 86618889HCID 86618889, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of 0.59 g of tert-butyl {3-[3-(3-methoxypropyl)-1-methyl-1H-indol-5-ylmethyl]-4-methyl-1-oxiranylpentyl}carbamate (Example 3Ab) in 12 ml of methanol is admixed with 0.21 g of sodium azide and 0.12 g of ammonium chloride and stirred at reflux over 6 hours. The reaction mixture is cooled, poured onto ice-water and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is identified on the basis of the Rf value from the residue.

Workup

  1. temperatureat reflux over 6 hours
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto ice-water
  4. extractionextracted with tert-butyl methyl ether (2×)
  5. washThe combined organic phases are washed with water and brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-94620e304fb64f9786f61a612dabe556
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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