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Cesium carbonate → Methyl 6-(benzenesulphonylmethyl)-2-[2-(t-butoxycarbonylamino)ethylamino]-3-(furan-3-yl)benzoate

HRID 2177785
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HRID 2177785 반응식
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15](OS(C(F)(F)F)(=O)=O)[C:14]([C:29]3[CH:33]=[CH:32][O:31][CH:30]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:34]([O:38][C:39]([NH:41][CH2:42][CH2:43][NH2:44])=[O:40])([CH3:37])([CH3:36])[CH3:35].C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([NH:44][CH2:43][CH2:42][NH:41][C:39]([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:40])[C:14]([C:29]3[CH:33]=[CH:32][O:31][CH:30]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 187201N-BOC-ethylenediamineHCID 634876Binap, (A+-)-HCID 86677115Methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(trifluoromethanesulphonyloxy)benzoate2회

생성물 1

HCID 67108007Methyl 6-(benzenesulphonylmethyl)-2-[2-(t-butoxycarbonylamino)ethylamino]-3-(furan-3-yl)benzoate수율 45.1%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

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온도
100 °C

실험 절차

A solution of methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(trifluoromethanesulphonyloxy)benzoate (Intermediate 123, 0.05 g), N-(t-butoxycarbonyl)ethylenediamine (0.048 g), palladium acetate (0.006 g), cesium carbonate (0.065 g) and (+/−)BINAP (0.034 g) in toluene (1.5 ml) was stirred and heated at 100° C., under nitrogen for 20 hours. After cooling, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 10-35%, to give methyl 6-(benzenesulphonylmethyl)-2-[2-(t-butoxycarbonylamino)ethylamino]-3-(furan-3-yl)benzoate (0.023 g) as a yellow gum.

후처리

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between water and ethyl acetate
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography on silica
  7. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 10-35%

출처 및 근거

ORD 기록
ord-a8269728bd714725a5877770542b4a11
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09067905B2

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