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

HRID 2177693ノート

反応式

HRID 2177693 の反応式
[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

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 67107629Ethyl 6-benzenesulphonylmethyl-3-(furan-3-yl)-2-hydroxybenzoate2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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.

後処理

  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%

出典と根拠

ORDレコード
ord-443c723fcef444ccbc4eb99a34c1d478
出典データセット
uspto-grants-2015_06
特許番号
US09067905B2

反応ノート

読み込み中…