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

HRID 1683990

Reaktionsgleichung

Reaktionsgleichung von HRID 1683990
[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

Komponenten

5

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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)

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-4582306753c74139b39e5a5ea654d00c
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05639780

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