4-Toluenesulfonyl chloride → HCID 86748025, compound

HRID 1729326Notes

Reaction equation

HRID 1729326 reaction equation
[CH2:1]([O:8][C:9](=[O:27])[CH:10]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[N:11]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:12][CH2:13][CH2:14]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[N-:50]=[N+:51]=[N-:52].[Na+]>N1C=CC=CC=1.CCOCC.CN(C=O)C.O.[Cl-].[Na+].O>[CH2:1]([O:8][C:9](=[O:27])[CH:10]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[N:11]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:12][CH2:13][CH2:14][N:50]=[N+:51]=[N-:52])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 33557Sodium AzideHCID 85570p-ToluenesulfonateHCID 86748026HCID 86748026, compound

Product 1

HCID 86748025HCID 86748025, compound

Reagents, catalysts & solvents 4

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent2×HCID 21962138N,N-Dimethylformamide--water (1/1)SolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

BOC-(2-isobutyl)-3-hydroxypropyl glycine benzyl ester (0.17 g, 0.45 mmol) is dissolved in pyridine (2 ml), cooled to 0° C., and p-toluenesulfonyl chloride (0.25 g, 1.31 mmol) is added. The mixture is then stirred at room temperature for 16 hours, diluted with ether, and the organic layer washed with 1N HCl, 10% copper sulfate solution, brine. The organic layer is dried over magnesium sulfate, filtered, concentrated in vacuo to give the tosylated product. The primary tosylate (0.23 g, 0.43 mmol) is dissolved in DMF/water (10:1) (2 ml) and sodium azide (0.29 g, 4.46 mmol) is added. The mixture is heated at 90° C. for four hours, cooled, diluted with ether and poured into brine. The organic layer is washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product is purified by flash chromatography, eluting with 10% ethyl aceate in hexanes to give BOC-(2-isobutyl)-3-azidopropyl glycine benzyl ester.

Workup

  1. washthe organic layer washed with 1N HCl, 10% copper sulfate solution, brine
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give the tosylated product
  6. temperatureThe mixture is heated at 90° C. for four hours
  7. temperaturecooled
  8. washThe organic layer is washed with water, brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe crude product is purified by flash chromatography
  13. washeluting with 10% ethyl aceate in hexanes

Sources & evidence

ORD record
ord-360ae8aeb2cd476fae9932301caec488
Source dataset
uspto-grants-1994_07
Patent number
US05332726

Reaction notes

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