Sodium Bicarbonate → (4S)-4-(phenylmethyl)-3-(2-phenylpropionyl)-2-oxazolidinone

HRID 1417805

반응식

HRID 1417805 반응식
[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

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 2760403Hydratropoyl chlorideHCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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) δ1.52, 2.58, 3.09, 4.08, 4.19, 4.75, 5.11, 6.95 and 7.31 δ.

후처리

  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

출처 및 근거

ORD 기록
ord-b5ee2018b6af4410848d2f8d1b473e73
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05877317

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