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

HRID 516043노트

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HRID 516043 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f00c4470f2e9408cad6cab212658c7d3
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108970B2

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