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Methyl 6-(benzenesulphonylmethyl)-2-(3-t-butyoxycarbonylamino-prop-1-yn-1-yl)-3-(furan-3-yl)benzoate → Methyl 6-(benzenesulphonylmethyl)-2-(3-t-butoxycarbonylaminopropyl)-3-(furan-3-yl)benzoate

HRID 2177792
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HRID 2177792 반응식
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([C:21]#[C:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:14]([C:32]3[CH:36]=[CH:35][O:34][CH:33]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>[Pd].C(O)C.C1COCC1>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[C:14]([C:32]3[CH:36]=[CH:35][O:34][CH:33]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 67107946Methyl 6-(benzenesulphonylmethyl)-2-(3-t-butyoxycarbonylamino-prop-1-yn-1-yl)-3-(furan-3-yl)benzoate2회HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 67107639Methyl 6-(benzenesulphonylmethyl)-2-(3-t-butoxycarbonylaminopropyl)-3-(furan-3-yl)benzoate수율 51.9%

시약·촉매·용매 3

HCID 23938Palladium촉매
HCID 702
Ethanol
용매
HCID 8028Tetrahydrofuran용매

실험 절차

10% Palladium on carbon (0.05 g) was added to a solution of methyl 6-(benzenesulphonylmethyl)-2-(3-t-butyoxycarbonylamino-prop-1-yn-1-yl)-3-(furan-3-yl)benzoate (Intermediate 132, 0.22 g) in ethanol (10 ml) and THF (10 ml) and the mixture was stirred at room temperature in an atmosphere of hydrogen (balloon) for 60 hours. The mixture was filtered through Celite and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 25-60% to give methyl 6-(benzenesulphonylmethyl)-2-(3-t-butoxycarbonylaminopropyl)-3-(furan-3-yl)benzoate (0.115 g) as a colourless gum.

후처리

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate was evaporated to dryness
  3. customThe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 25-60%

출처 및 근거

ORD 기록
ord-cb1c0d29a8d9489f8253289c2090503d
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09067905B2

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