N,N'-Dimethylethylenediamine → ethyl (R)-2-methanesulfonyl-4-(3-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)benzoate

HRID 2411153ノート

反応式

HRID 2411153 の反応式
I[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:3]=1.[CH3:17][C@@H:18]1[CH2:22][CH2:21][S:20](=[O:24])(=[O:23])[NH:19]1.CNCCNC.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.O.C1(C)C=CC=CC=1>[CH3:16][S:13]([C:4]1[CH:3]=[C:2]([N:19]2[C@H:18]([CH3:17])[CH2:22][CH2:21][S:20]2(=[O:24])=[O:23])[CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:15])=[O:14]

参加物

8

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 16664802(R)-3-methylisothiazolidine 1,1-dioxideHCID 71252507Ethyl 4-iodo-2-methanesulfonylbenzoate

生成物 1

HCID 71261164ethyl (R)-2-methanesulfonyl-4-(3-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)benzoate収率 51.7%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

To a mixture of ethyl 4-bromo-2-methanesulfonylbenzoate (13.88 g), sodium iodide (13.54 g) and copper(I) iodide (4.30% g) were added toluene (46 mL) and N,N′-dimethylethylenediamine (4.86 mL), and the mixture was stirred with heating under reflux for 8 hr under a nitrogen stream. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The solvent was evaporated from the organic layer, the obtained residue was purified by column chromatography (hexane:ethyl acetate) to give ethyl 4-iodo-2-methanesulfonylbenzoate (10.32 g). To a mixture of the obtained ethyl 4-iodo-2-methanesulfonylbenzoate (3.22 g), (R)-3-methylisothiazolidine 1,1-dioxide (1.23 g) described in Preparation Example 2, copper(I) iodide (4.30 g), N,N′-dimethylethylenediamine (0.92 mL) and potassium carbonate (2.52 g) was added toluene (9.2 mL), and the mixture was stirred with heating under reflux for 8 hr under a nitrogen stream. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The solvent was evaporated from the organic layer, and the obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (1.7 g).

後処理

  1. temperaturewith heating
  2. temperatureunder reflux for 8 hr under a nitrogen stream
  3. temperatureThe reaction mixture was cooled
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe solvent was evaporated from the organic layer
  6. customthe obtained residue was purified by column chromatography (hexane:ethyl acetate)

出典と根拠

ORDレコード
ord-26f015bf36e54cc5a55aa8c6cf042da9
出典データセット
uspto-grants-2014_08
特許番号
US08816079B2

反応ノート

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