Hydrochloric Acid → Acetoxymethyl 8-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-1,4-dioxaspiro[4.5]dec-6-ene-7-carboxylate

HRID 546351ノート

反応式

HRID 546351 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH:13]1[CH2:22][CH2:21][C:16]2([O:20][CH2:19][CH2:18][O:17]2)[CH:15]=[C:14]1[C:23]([OH:25])=[O:24])(=[O:12])=[O:11].[C:26]([O:29][CH2:30]Br)(=[O:28])[CH3:27].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>C(#N)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH:13]1[CH2:22][CH2:21][C:16]2([O:17][CH2:18][CH2:19][O:20]2)[CH:15]=[C:14]1[C:23]([O:25][CH2:30][O:29][C:26](=[O:28])[CH3:27])=[O:24])(=[O:12])=[O:11]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 68536Bromomethyl acetateHCID 671921038-[N-(2-Chloro-4-fluorophenyl)sulfamoyl]-1,4-dioxaspiro[4.5]dec-6-ene-7-carboxylic acid

生成物 1

HCID 57870890Acetoxymethyl 8-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-1,4-dioxaspiro[4.5]dec-6-ene-7-carboxylate収率 70.4%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6342Acetonitrile溶媒

実験手順

1 g (2.55 mmol) of 8-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-1,4-dioxaspiro[4.5]dec-6-ene-7-carboxylic acid obtained in Example 47a was dissolved in 20 ml of acetonitrile, and 0.50 ml (5.10 mmol) of bromomethyl acetate, 499 mg (1.53 mmol) of cesium carbonate and 471 mg (1.28 mmol) of tetrabutylammonium iodide were added thereto, followed by stirring for 1 hour at room temperature. 0.1 N hydrochloric acid was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was subjected to silica gel column chromatography (solvent; dichloromethane:methanol=49:1) to give 833 mg of the title compound as an amorphous substance (yield: 70%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationfollowed by concentration under reduced pressure

出典と根拠

ORDレコード
ord-f21cff1b25ea4ca9b8efdda1ee225f2f
出典データセット
uspto-grants-2011_05
特許番号
US07935835B2

反応ノート

読み込み中…