Cesium carbonate → Ethyl 6-(benzenesulphonylmethyl)-2-[2-(t-butoxycarbonyl)aminoethoxy]-3-(furan-3-yl)benzoate

HRID 2177693노트

반응식

HRID 2177693 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10]Br)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:12]1([S:18]([CH2:21][C:22]2[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:26]([OH:33])[C:25]([C:34]3[CH:38]=[CH:37][O:36][CH:35]=3)=[CH:24][CH:23]=2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:12]1([S:18]([CH2:21][C:22]2[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:26]([O:33][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:25]([C:34]3[CH:38]=[CH:37][O:36][CH:35]=3)=[CH:24][CH:23]=2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 67107629Ethyl 6-benzenesulphonylmethyl-3-(furan-3-yl)-2-hydroxybenzoate2회

생성물 1

HCID 67107565Ethyl 6-(benzenesulphonylmethyl)-2-[2-(t-butoxycarbonyl)aminoethoxy]-3-(furan-3-yl)benzoate수율 45.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A solution of 2-[N-(t-butoxycarbonyl)amino]ethyl bromide (0.032 g) in DMF (0.5 ml) was added to a stirred cooled solution of ethyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-hydroxybenzoate (Intermediate 36, 0.05 g) and cesium carbonate (0.065 g) in DMF (0.5 ml) at 0° C. The resultant mixture was allowed to warm to room temperature, stirred for 3 hours then partitioned between ethyl acetate and water. The organic layer was washed with water, dried (MgSO4) 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 20-25% to give ethyl 6-(benzenesulphonylmethyl)-2-[2-(t-butoxycarbonyl)amino-ethoxy]-3-(furan-3-yl)-benzoate (0.031 g) as a colourless gum.

후처리

  1. customthen partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water
  3. dry with materialdried (MgSO4)
  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 20-25%

출처 및 근거

ORD 기록
ord-443c723fcef444ccbc4eb99a34c1d478
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067905B2

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