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

HRID 1683990

反応式

HRID 1683990 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-4582306753c74139b39e5a5ea654d00c
出典データセット
uspto-grants-1997_06
特許番号
US05639780

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