Ammonium Chloride → HCID 22928354, compound

HRID 751464Notes

Reaction equation

HRID 751464 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:9][CH:8]2[CH:6]([O:7]2)[CH2:5][N:4]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)(=[O:12])=[O:11])[CH2:3]1.[N-:20]=[N+:21]=[N-:22].[Na+].[NH4+].[Cl-]>CO.O>[N:20]([CH:8]1[CH2:9][C:2]([CH3:19])([CH3:1])[CH2:3][N:4]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)(=[O:12])=[O:11])[CH2:5][CH:6]1[OH:7])=[N+:21]=[N-:22]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 53685855HCID 53685855, compound

Product 1

HCID 22928354HCID 22928354, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

5,5-Dimethyl-3-(pyridine-2-sulfonyl)-8-oxa-3-aza-bicyclo[5.1.0]octane from Example 92e (1.2 g, 4.3 mmol) was dissolved in the mixture of 7 ml MeOH and 1 ml H2O. NaN3 (0.83 g, 13 mmol) and NH4Cl (0.7 g, 13 mmol) were added to the solution. The resulting mixture was refluxed overnight. After the removal of MeOH, the residue was diluted in EtOAc and washed with 10% NaHCO3 and brine. Purified on column chromatography gave 0.4 g 4-azido-6,6-dimethyl-1-(pyridine-2-sulfonyl)-azepan-3-ol (yield 29%); MS (M+H+): 326.2; 1H-NMR (400 MHz, CDCl3): •8.68-8.67(m, 1H), 8.05-7.90(m, 2H), 7.53-7.50(m, 1H), 3.75-3.60(m, 3H), 3.49-3.30(m, 3H), 1.73-1.66(m, 1H), 1.56-1.52(d, 1H), 1.07(s, 3H), 0.99(s, 3H)

Workup

  1. temperatureThe resulting mixture was refluxed overnight
  2. customAfter the removal of MeOH
  3. additionthe residue was diluted in EtOAc
  4. washwashed with 10% NaHCO3 and brine
  5. customPurified on column chromatography

Sources & evidence

ORD record
ord-29254f8f327b4615bb01d9e9a0588840
Source dataset
uspto-grants-2008_07
Patent number
US07405209B2

Reaction notes

Loading…