Pyridine → (S)-Benzyl 2-(2-oxooxazolidin-4-YL)acetate

HRID 1631289

反応式

HRID 1631289 の反応式
C(O[C:6]([NH:8][C@H:9]([CH2:21][OH:22])[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:7])(C)(C)C.C1(C)C=CC=CC=1.N1C=CC=CC=1.C1(C)C=CC(S(OS(C2C=CC(C)=CC=2)(=O)=O)(=O)=O)=CC=1>ClC(Cl)C.ClCCl>[O:7]=[C:6]1[NH:8][C@@H:9]([CH2:10][C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])[CH2:21][O:22]1

参加物

7

反応物 4

HCID 1049PyridineHCID 1140TolueneHCID 77773Toluene-p-sulphonic anhydride2 回HCID 10040985Phenylmethyl (3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxybutanoate

生成物 1

HCID 11241814(S)-Benzyl 2-(2-oxooxazolidin-4-YL)acetate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 63651,1-Dichloroethane溶媒

反応条件

温度
0 °C

実験手順

The alcohol 2 (500 mg, 1.616 mmol) was azeotroped with toluene, and then dissolved in dichloroethane (5 mL). Pyridine (1.44 mL, 17.78 mmol) was added and the mixture was cooled to 0° C. Anhydrous p-toluenesulfonic anhydride (580 mg, 1.778 mmol) was added and the mixture was warmed to room temperature and stirred for 1 hour. A condenser was adapted to the reaction flask and the mixture heated to 90° C. for two hours. Added additional 0.5 equivalents (290 mg) of p-toluenesulfonic anhydride and heated at 90° C. overnight. The mixture was cooled, diluted with dichloromethane and washed with 1 N HCl (2×3 mL), then water. The organic layer was dried with sodium sulfate and filtered over a small silica plug, rinsing with ethyl acetate. The solvents were removed in vacuo to afford an oil that crystallizes. LC-MS m/z=253 (M+NH4+).

後処理

  1. temperaturethe mixture was warmed to room temperature
  2. customA condenser was adapted to the reaction flask
  3. temperaturethe mixture heated to 90° C. for two hours
  4. temperatureheated at 90° C. overnight
  5. temperatureThe mixture was cooled
  6. washwashed with 1 N HCl (2×3 mL)
  7. dry with materialThe organic layer was dried with sodium sulfate
  8. filtrationfiltered over a small silica plug
  9. washrinsing with ethyl acetate
  10. customThe solvents were removed in vacuo
  11. customto afford an oil
  12. customthat crystallizes

出典と根拠

ORDレコード
ord-e28ebf69e6b040f8bf931db90e5702c5
出典データセット
uspto-grants-2014_07
特許番号
US08791162B2

関連ノート

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