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N-Hydroxyphthalimide → N-{4-[2-(4-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl) oxy]methyl}phenyl)ethyl]-1,3-thiazol-2-yl}acetamide

HRID 1246464
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HRID 1246464 반응식
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:12]=[C:13]([NH:16][C:17](=[O:19])[CH3:18])[S:14][CH:15]=2)=[CH:5][CH:4]=1.O[N:21]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]1=[O:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C(=O)([O-])O.[Na+]>O1CCCC1>[O:31]=[C:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:29](=[O:30])[N:21]1[O:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:12]=[C:13]([NH:16][C:17](=[O:19])[CH3:18])[S:14][CH:15]=2)=[CH:5][CH:4]=1
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참가 물질

7

반응물 5

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 516892Sodium BicarbonateHCID 21914951N-(4-{2-[4-(hydroxymethyl)phenyl]ethyl}thiazol-2-yl)acetamide

생성물 1

HCID 21915019
N-{4-[2-(4-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl) oxy]methyl}phenyl)ethyl]-1,3-thiazol-2-yl}acetamide
수율 57.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

N-(4-{2-[4-(Hydroxymethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (250 mg), 2-hydroxy-1H-isoindole-1,3(2H)-dione (155 mg), triphenylphosphine (249 mg) and tetrahydrofuran (5 ml) were combined under nitrogen atmosphere, and then diethyl azodicarboxylate (0.15 ml) was added to the solution at 0° C. The reaction mixture was stirred at room temperature for 6 hours, poured into saturated sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel with chloroform/methanol (20:1) as an eluent, and triturated with ethyl acetate to give N-{4-[2-(4-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}phenyl)ethyl]-1,3-thiazol-2-yl}acetamide (218.2 mg) as a colorless solid.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography over silica gel with chloroform/methanol (20:1) as an eluent
  6. customtriturated with ethyl acetate

출처 및 근거

ORD 기록
ord-a2b55341dd474d149b51421f0d5f9e0f
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07125901B2

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