Sodium Azide → (S)-6-(2-azidoethyl)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one

HRID 2091519ノート

反応式

HRID 2091519 の反応式
CS(O[CH2:6][CH2:7][C@@:8]1([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:16])[CH2:10][CH2:9]1)(=O)=O.[N-:28]=[N+:29]=[N-:30].[Na+]>CN(C=O)C>[N:28]([CH2:6][CH2:7][C@@:8]1([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:16])[CH2:10][CH2:9]1)=[N+:29]=[N-:30]

参加物

4

反応物 2

HCID 33557Sodium AzideHCID 866587272-((S)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl methanesulfonate

生成物 1

HCID 58485263(S)-6-(2-azidoethyl)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one収率 93%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-((S)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl methanesulfonate (273 mg, 0.68 mmol) in DMF (5 mL) was added NaN3 (133 mg, 2.04 mmol), and the mixture was refluxed overnight. The reaction was quenched with H2O, and the pH of the mixture was adjusted to >9 with 1N aq NaOH. The mixture was extracted with EtOAc (3×). The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated to give (S)-6-(2-azidoethyl)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (219 mg, 93%). 1H NMR (CDCl3): 0.61-0.69 (s, 9H), 1.02-1.08 (d, 3H), 1.98-2.14 (m, 3H), 2.23-2.32 (m, 1H), 2.51-2.61 (m, 1H), 2.91-3.02 (m, 1H), 3.06-3.13 (m, 1H), 3.41-3.52 (m, 1H), 4.33-4.42 (m, 1H), 6.98-7.03 (m, 2H), 7.21-7.24 (m, 2H).

後処理

  1. temperaturethe mixture was refluxed overnight
  2. customThe reaction was quenched with H2O
  3. extractionThe mixture was extracted with EtOAc (3×)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-fccc06722d494fb5ae7ddaa3e9040c75
出典データセット
uspto-grants-2013_05
特許番号
US08440658B2

反応ノート

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