Triphenylphosphine Oxide → 7-(Benzyloxy)-2-(4,5-dihydro-1,3-thiazol-2-yl)-1H-indole

HRID 1851458노트

반응식

HRID 1851458 반응식
C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH2:36]([O:43][C:44]1[CH:45]=[CH:46][CH:47]=[C:48]2[C:52]=1[NH:51][C:50]([C:53]([NH:55][CH2:56][CH2:57][S:58]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)=[CH:49]2)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>ClCCl>[CH2:36]([O:43][C:44]1[CH:45]=[CH:46][CH:47]=[C:48]2[C:52]=1[NH:51][C:50]([C:53]1[S:58][CH2:57][CH2:56][N:55]=1)=[CH:49]2)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

참가 물질

5

반응물 3

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 579018537-(Benzyloxy)-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide

생성물 1

HCID 579016087-(Benzyloxy)-2-(4,5-dihydro-1,3-thiazol-2-yl)-1H-indole수율 27%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of triphenylphosphine oxide (4.70 g) in dichloromethane (20 mL) was slowly added trifluoromethanesulfonic anhydride (1.42 mL) at 0° C. The mixture was stirred for 10 min, and 7-(benzyloxy)-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide (1.60 g) was added. The reaction mixture was stirred at room temperature for 3 hr and concentrated. Saturated aqueous sodium hydrogen carbonate was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography and the title compound (0.23 g, yield 27%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:20→1:2, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point 129-130° C.

후처리

  1. customat 0° C
  2. stirringThe reaction mixture was stirred at room temperature for 3 hr
  3. concentrationconcentrated
  4. additionSaturated aqueous sodium hydrogen carbonate was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c3c5b5ad290f4e00a2fce1303f82b0f3
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957070B2

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