碳酸氢钠 → (4S)-4-(phenylmethyl)-3-(2-phenylpropionyl)-2-oxazolidinone

HRID 368824

反应方程式

HRID 368824 反应方程式
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:19]1([CH:25]([CH3:29])[C:26](Cl)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)(O)[O-].[Na+]>C1COCC1>[C:2]1([CH2:1][C@H:8]2[CH2:12][O:11][C:10](=[O:13])[N:9]2[C:26](=[O:27])[CH:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:29])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参与物

6

反应物 4

HCID 516892碳酸氢钠HCID 736225(S)-4-苄基-2-唑烷酮HCID 27604032-苯基丙酰氯HCID 178418339正丁基锂

产物 1

HCID 56980759(4S)-4-(phenylmethyl)-3-(2-phenylpropionyl)-2-oxazolidinone

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂2 次

实验过程

A mixture of (4S)-(-)-4-benzyl-2-oxazolidinone (3.903 g, 22.0 mmol) in THF (23 ml) is cooled at -78° and butyl lithium (1.6M in hexane, 14.7 ml, 23.5 mmol) is added. The mixture is stirred for 50 min and then the portion of 2-phenylpropionic acid chloride (XL) from above, in THF (8 ml) is added dropwise to the mixture. The mixture is stirred for 1 hr at -78° and then allowed to warm to 20-25°. Saturated aqueous sodium bicarbonate solution (100 ml) is added and the phases separated. The aqueous phase is washed with ether and the combined organic phases are then washed several times with saturated aqueous sodium bicarbonate followed by a saline wash. The organic phase is dried over magnesium sulfate and concentrated. The resulting diastereomers are separated on silica gel eluting with ethyl acetate/hexane (7/93) followed by ethyl acetate/hexane (12/88). The appropriate fractions are pooled and concentrated to give (4S)-4-(phenylmethyl)-3-(2-phenylpropionyl)-2-oxazolidinone (XLI, Isomer I, less polar isomer), NMR (CDCl3) 1.55, 2.79, 3.35, 4.09, 4.58, 5.12 and 7.30 δ; and (4S)-4-(phenylmethyl)-3-(2-phenylpropionyl)-2-oxazolidinone (XLII, Isomer II, more polar isomer), NMR (CDCl3) δ 1.52, 2.58, 3.09, 4.08, 4.19, 4.75, 5.11, 6.95 and 7.31 δ.

后处理

  1. temperatureis cooled at -78°
  2. stirringThe mixture is stirred for 1 hr at -78°
  3. temperatureto warm to 20-25°
  4. customthe phases separated
  5. washThe aqueous phase is washed with ether
  6. washthe combined organic phases are then washed several times with saturated aqueous sodium bicarbonate
  7. washwash
  8. dry with materialThe organic phase is dried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe resulting diastereomers are separated on silica gel eluting with ethyl acetate/hexane (7/93)
  11. concentrationconcentrated

来源与证据

ORD记录
ord-80dd2d94767b435f9c957400670879fd
来源数据集
uspto-grants-2000_10
专利号
US06133446

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