Water → 2-Azidohexadecanoic acid

HRID 2210840Notes

Reaction equation

HRID 2210840 reaction equation
Br[CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:3]([OH:5])=[O:4].[N-:20]=[N+:21]=[N-:22].[Na+].O>CN(C)C=O>[N:20]([CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:3]([OH:5])=[O:4])=[N+:21]=[N-:22]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 821452-Bromohexadecanoic acid

Product 1

HCID 190472092-Azidohexadecanoic acidYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To the solution of 2-bromohexadecanoic acid (1.00 g) in N,N-dimethylformamide (DMF, 15 ml) was added sodium azide (0.86 g), and the mixture was stirred at 80° C. for 12 hours. To the reaction mixture, after having been cooled to room temperature, was then added water. The mixture was extracted with ethyl acetate, and the ethyl acetate layer was separated, washed twice with brine, dried over anhydrous sodium sulfate. The solvent was removed by distillation to give 2-azidohexadecanoic acid (0.73 g). To the solution of 2-azidohexadecanoic acid in DMF were added N-hydroxysuccinimide (74 mg) and N,N'-dicyclohexylcarbodiimide (146 mg), and the mixture was stirred for 12 hours. Precipitates produced was removed by filtration, and the filtrate was concentrated to give the active ester of 2-azidohexadecanoic acid. To the active ester in DMF were further added 6-(4'-N-glycylspicaminyl-amino)purine hydrochloride (246 mg) and triethylamine (0.72 ml), and the mixture was stirred for 12 hours. The solvent was removed by distillation, and the residue was subjected to chromatography on a silica gel column with an eluent system of chloroform-methanol (6:1) to give SPK229 in the yield of 185 mg.

Workup

  1. temperatureTo the reaction mixture, after having been cooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. customthe ethyl acetate layer was separated
  4. washwashed twice with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation

Sources & evidence

ORD record
ord-3d50cdd946d446fe8a1119125a41b18e
Source dataset
uspto-grants-1995_10
Patent number
US05461036

Reaction notes

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