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Water → 8-(1-(1-((Tert-butyldimethylsilyl)oxy)-4-methyl-1,3-dihydroisobenzofuran-5-yl)-1-hydroxy-2-methylpropan-2-yl)-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

HRID 1848559
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HRID 1848559 반응식
[Si:1]([O:8][CH:9]1[C:17]2[C:12](=[C:13]([CH3:34])[C:14]([CH:18]([OH:33])[C:19]([N:22]3[CH2:32][CH2:31][C:25]4([C:29](=[O:30])[NH:28][CH2:27][CH2:26]4)[CH2:24][CH2:23]3)([CH3:21])[CH3:20])=[CH:15][CH:16]=2)[CH2:11][O:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].FC(F)(F)S(O[C:41]1[CH2:42][O:43][C:44](=[O:47])[C:45]=1[CH3:46])(=O)=O.C(=O)([O-])[O-].[K+].[K+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.O>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Si:1]([O:8][CH:9]1[C:17]2[C:12](=[C:13]([CH3:34])[C:14]([CH:18]([OH:33])[C:19]([N:22]3[CH2:23][CH2:24][C:25]4([C:29](=[O:30])[N:28]([C:41]5[CH2:42][O:43][C:44](=[O:47])[C:45]=5[CH3:46])[CH2:27][CH2:26]4)[CH2:31][CH2:32]3)([CH3:21])[CH3:20])=[CH:15][CH:16]=2)[CH2:11][O:10]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]
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참가 물질

8

반응물 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 108901884-Methyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonateHCID 867095398-(1-(1-((Tert-butyldimethylsilyl)oxy)-4-methyl-1,3-dihydroisobenzofuran-5-yl)-1-hydroxy-2-methylpropan-2-yl)-2,8-diazaspiro[4.5]decan-1-one

생성물 1

HCID 867095418-(1-(1-((Tert-butyldimethylsilyl)oxy)-4-methyl-1,3-dihydroisobenzofuran-5-yl)-1-hydroxy-2-methylpropan-2-yl)-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

반응 조건

온도
70 °C

실험 절차

To a mixture of 8-(1-(1-((tert-butyldimethylsilyl)oxy)-4-methyl-1,3-dihydroisobenzofuran-5-yl)-1-hydroxy-2-methylpropan-2-yl)-2,8-diazaspiro[4.5]decan-1-one (1.35 g, 2.76 mmol), 4-methyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate (I-9) (0.884 g, 3.59 mmol) in toluene (40 mL) was added potassium carbonate (0.764 g, 5.52 mmol), Xantphos (0.320 g, 0.552 mmol), and water (0.149 mL, 8.29 mmol). The mixture was flushed with nitrogen for 20 min before addition of palladium (II) acetate (0.062 g, 0.276 mmol). The resulting mixture was heated at 70° C. overnight. After filtration the filtrate was concentrated and the residue was purified on silica gel column using methanol/methylene chloride as eluting solvents to give the title compound. LC/MS: (M+1−114)+: 471.22.

후처리

  1. filtrationAfter filtration the filtrate
  2. concentrationwas concentrated
  3. customthe residue was purified on silica gel column
  4. washas eluting solvents

출처 및 근거

ORD 기록
ord-b2c39e94edcb4648a1d59283e6f7620c
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08952166B2

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