Triethylamine → (R)-tert-Butyl 1-azido-3-ethoxypropan-2-ylcarbamate

HRID 2092808Notes

Reaction equation

HRID 2092808 reaction equation
CS(Cl)(=O)=O.[CH2:6]([O:8][CH2:9][C@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:11]O)[CH3:7].CCN(CC)CC.[N-:28]=[N+:29]=[N-:30].[Na+]>C(Cl)Cl.CCOC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[N:28]([CH2:11][C@@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9][O:8][CH2:6][CH3:7])=[N+:29]=[N-:30]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 45092315(R)-tert-Butyl 1-ethoxy-3-hydroxypropan-2-ylcarbamate

Product 1

HCID 86654722(R)-tert-Butyl 1-azido-3-ethoxypropan-2-ylcarbamateYield 67.3%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

Methanesulfonyl chloride (0.851 mL, 10.95 mmol) in DCM (1 mL) was added to a solution of (R)-tert-butyl 1-ethoxy-3-hydroxypropan-2-ylcarbamate (1.6 g, 7.30 mmol) and Et3N (1.538 mL, 10.95 mmol) in DCM (10 mL) at 0° C. After stirring at RT for 1 h, the mixture was diluted with EtOAc. The organic layer was washed with saturated aq NaHCO3 solution, dried, and concentrated in vacuo. The residue was dissolved in DMF (10.00 mL). Sodium azide (2.372 g, 36.5 mmol) and tetrabutylammonium iodide (0.270 g, 0.730 mmol) were added, and the reaction mixture was stirred at 75° C. for 4 h. After cooling to RT, the mixture was diluted with EtOAc. The organic layer was washed with saturated aq NaHCO3, dried, and concentrated in vacuo to give the title compound (1.2 g, 67%). [M+H] calc'd for C10H20N4O3, 245. found, 245.

Workup

  1. washThe organic layer was washed with saturated aq NaHCO3 solution
  2. customdried
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in DMF (10.00 mL)
  5. stirringthe reaction mixture was stirred at 75° C. for 4 h
  6. temperatureAfter cooling to RT
  7. washThe organic layer was washed with saturated aq NaHCO3
  8. customdried
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be22364fbd804bc39c34db4286da9353
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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