Hydrogen Peroxide → 4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-3-methylbutanoic acid

HRID 1683990

반응식

HRID 1683990 반응식
[Br:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][CH:19]([CH3:32])[CH2:20][C:21](N3[C@H](C(C)C)COC3=O)=[O:22])=[C:8]2[CH3:33])=[CH:4][CH:3]=1.[OH:36]O.[Li+].[OH-]>C1COCC1>[Br:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][CH:19]([CH3:32])[CH2:20][C:21]([OH:22])=[O:36])=[C:8]2[CH3:33])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 54133645(4R)-N-[4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-3-methylbutanoyl]-4-isopropyl-2-oxazolidinone

생성물 1

HCID 98673334-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-3-methylbutanoic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To the oxazolidinone from Step 7, isomer A (295 mg, 0.54 mmol) in THF (10 mL) at -10° C. was added 30% H2O2 (0.5 mL) followed by 1M aqueous LiOH (3 mL). The mixture was stirred at 0° C. for 45 min, and was then cooled to -10° C. to be quenched by careful addition of 1M aqueous Na2S2O5 (10 mL). The mixture was acidified (6M HCl, 1 mL) and the product was extracted with EtOAc. The organic layer was washed with H2O and brine, and was then dried (MgSO4), and filtered. After removal of the solvent, the crude product was purified by flash chromatography (1:5 EtOAc/hexane followed by 1:2 EtOAc/hexane). The resulting off-white solid was stirred vigorously with 1:10 EtOAc/hexane for 2 h to give, after filtration, 188 mg of the title compound. [α]D =+4.6° (c=1, acetone)

후처리

  1. temperaturewas then cooled to -10° C.
  2. customto be quenched by careful addition of 1M aqueous Na2S2O5 (10 mL)
  3. extractionthe product was extracted with EtOAc
  4. washThe organic layer was washed with H2O and brine
  5. dry with materialwas then dried (MgSO4)
  6. filtrationfiltered
  7. customAfter removal of the solvent
  8. customthe crude product was purified by flash chromatography (1:5 EtOAc/hexane followed by 1:2 EtOAc/hexane)
  9. stirringThe resulting off-white solid was stirred vigorously with 1:10 EtOAc/hexane for 2 h
  10. customto give
  11. filtrationafter filtration, 188 mg of the title compound
  12. custom[α]D =+4.6° (c=1, acetone)

출처 및 근거

ORD 기록
ord-4582306753c74139b39e5a5ea654d00c
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05639780

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