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

HRID 711504ノート

反応式

HRID 711504 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 67553Tetrabutylammonium Iodide触媒HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d6d2c7da40ee4e779ac001f15c8e4896
出典データセット
uspto-grants-2015_11
特許番号
US09181255B2

反応ノート

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