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Potassium Iodide → methyl (S)-4-(3-benzyloxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-methoxybenzoate

HRID 2411133
ノート
印刷プレビュー

反応式

HRID 2411133 の反応式
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[CH2:14]([O:21][CH2:22][C@@H:23]1[CH2:27][CH2:26][S:25](=[O:29])(=[O:28])[NH:24]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].CNCCNC>[Cu]I.O.C1(C)C=CC=CC=1>[CH2:14]([O:21][CH2:22][C@@H:23]1[CH2:27][CH2:26][S:25](=[O:29])(=[O:28])[N:24]1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 4875Potassium IodideHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 15128242Methyl 4-bromo-2-methoxybenzoateHCID 16664117(S)-3-benzyloxymethylisothiazolidine 1,1-dioxide

生成物 1

HCID 71261160methyl (S)-4-(3-benzyloxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-methoxybenzoate
収率 93.8%

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 methyl 4-bromo-2-methoxybenzoate (245 mg), (S)-3-benzyloxymethylisothiazolidine 1,1-dioxide (241 mg) described in Preparation Example 1, potassium carbonate (276 mg), potassium iodide (166 mg) and copper(I) iodide (95 mg) were added toluene (3 mL) and N,N′-dimethylethylenediamine (110 μL), and the mixture was stirred with heating under reflux for 8 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (380 mg).

後処理

  1. temperaturewith heating
  2. temperatureunder reflux for 8 hr
  3. temperatureThe reaction mixture was cooled
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

出典と根拠

ORDレコード
ord-6df5695cb0704eb685736d6f4522aa0e
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08816079B2

反応ノート

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