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Toluene → N-[4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-2(R),3(S)-dimethylbutanoyl]-4(R)-isopropyl-2-oxazolidinone

HRID 1683992
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HRID 1683992 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]([N:23]3[C@H:27]([CH:28]([CH3:30])[CH3:29])[CH2:26][O:25][C:24]3=[O:31])=[O:22])=[C:8]2[CH3:33])=[CH:4][CH:3]=1.[CH3:36][Si]([N-][Si](C)(C)C)(C)C.[K+].C1(C)C=CC=CC=1.CI>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][C@H:19]([CH3:32])[C@@H:20]([CH3:36])[C:21]([N:23]3[C@H:27]([CH:28]([CH3:29])[CH3:30])[CH2:26][O:25][C:24]3=[O:31])=[O:22])=[C:8]2[CH3:33])=[CH:4][CH:3]=1
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참가 물질

6

반응물 4

HCID 1140TolueneHCID 6328Methyl iodideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 54133645(4R)-N-[4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-3-methylbutanoyl]-4-isopropyl-2-oxazolidinone

생성물 1

HCID 22873808N-[4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-2(R),3(S)-dimethylbutanoyl]-4(R)-isopropyl-2-oxazolidinone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-40 °C

실험 절차

To the imide of Example 7, Step 7, isomer A (200 mg, 0.369 mmol) dissolved in THF (2.0 mL) at -78° C. was added a solution of KHMDS (0.5 mL) in toluene (1.10 mL, 0,660 mmol). The temperature was then increased slowly to -40° C. To the mixture recooled at -78° C. was added MeI (100 mL). The temperature was allowed to wam slowly to -40° and the reaction was quenched by the addition of 25% aqueous solution of NH4OAc. The mixture was extracted with EtOAc, dried over Na2SO4, evaporated in vacuo and purified by flash chromatography (20% EtOAc in hexane) to afford the title product (100 mg).

후처리

  1. customrecooled at -78° C.
  2. customto wam slowly to -40°
  3. customthe reaction was quenched by the addition of 25% aqueous solution of NH4OAc
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo
  7. custompurified by flash chromatography (20% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-898c1d2116914a968fb1578d7de577dc
출처 데이터셋
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05639780

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