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

HRID 2411133
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HRID 2411133 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-6df5695cb0704eb685736d6f4522aa0e
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08816079B2

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