Lithium Hexamethyldisilazide → (4R,5S)-3-((R)-3-cyclopentyl-2-phenyl-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one

HRID 889592노트

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HRID 889592 반응식
[CH3:1][C@@H:2]1[C@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4](=[O:13])[N:3]1[C:14](=[O:22])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH:33]1([CH2:38]OS(C(F)(F)F)(=O)=O)[CH2:37][CH2:36][CH2:35][CH2:34]1>C1COCC1.C(OCC)(=O)C>[CH:33]1([CH2:38][C@H:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:14]([N:3]2[C@H:2]([CH3:1])[C@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:5][C:4]2=[O:13])=[O:22])[CH2:37][CH2:36][CH2:35][CH2:34]1

참가 물질

6

반응물 3

HCID 2733832Lithium HexamethyldisilazideHCID 11748453(4R,5S)-4-methyl-5-phenyl-3-phenylacetyl-oxazolidin-2-oneHCID 57617550Trifluoromethanesulfonic acid cyclopentylmethyl ester

생성물 1

HCID 67024850(4R,5S)-3-((R)-3-cyclopentyl-2-phenyl-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

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온도
-78 °C

실험 절차

The title A compound, (4R,5S)-4-methyl-5-phenyl-3-phenylacetyl-oxazolidin-2-one (5.00 g, 16.93 mmol) is dissolved in anhydrous THF (50 mL) and cooled to −78° C. Lithium bis(trimethylsilyl)amide (1 M in THF, 16.93 mL, 16.93 mmol) is added dropwise over 10 min. To this is added a solution of the title B compound, trifluoromethanesulfonic acid cyclopentylmethyl ester (3.93 g, 16.93 mmol) in anhydrous THF (15 mL). The reaction is stirred at −78° C. for 10 min, then the cold bath is removed. The reaction is allowed to stir and warm to RT. After one hour, the reaction is concentrated to remove the solvent, resulting in a yellow oil. This is dissolved in ethyl acetate (300 mL) and washed with water (2×200 mL). The organic solution is dried over anhydrous sodium sulfate, filtered, and concentrated to a yellow oil. This is recrystallized from hexanes to afford (4R,5S)-3-((R)-3-cyclopentyl-2-phenyl-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one as a white solid: 1H NMR (400 MHz, DMSO-D6) 0.8 (d, J=6.6 Hz, 3 H) 1.1 (d, J=16.2 Hz, 2 H) 1.4 (m, 2 H) 1.5 (d, J=5.8 Hz, 2 H) 1.6 (s, 2 H) 1.8 (d, J=7.1 Hz, 2 H) 2.0 (d, J=13.4 Hz, 1 H) 4.8 (s, 1 H) 5.1 (s, 1 H) 5.7 (d, J=7.1 Hz, 1 H) 7.3 (s, 1 H) 7.4 (m, 9 H); LC/MS 378.2 (M+1).

후처리

  1. customthe cold bath is removed
  2. stirringto stir
  3. temperaturewarm to RT
  4. waitAfter one hour
  5. concentrationthe reaction is concentrated
  6. customto remove the solvent
  7. customresulting in a yellow oil
  8. washwashed with water (2×200 mL)
  9. dry with materialThe organic solution is dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated to a yellow oil
  12. customThis is recrystallized from hexanes

출처 및 근거

ORD 기록
ord-f4e736d1ae5a4339ba9d1c32d297bc8d
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252931B2

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