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Potassium Carbonate → Methyl 2-{[(4-ethoxyphenyl)sulfonyl]-4-methylanilino}propanoate

HRID 971320
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HRID 971320 반응식
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)[CH3:2].[CH3:21][O:22][C:23](=[O:27])[CH:24](Br)[CH3:25].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([S:10]([N:13]([CH:24]([CH3:25])[C:23]([O:22][CH3:21])=[O:27])[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:11])=[O:12])=[CH:8][CH:9]=1)[CH3:2]
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 9250104-ethoxy-N-(4-methylphenyl)benzenesulfonamide

생성물 1

HCID 11588923Methyl 2-{[(4-ethoxyphenyl)sulfonyl]-4-methylanilino}propanoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

The crude N-aryl-benzenesulfonamide building block XIII, e.g. 4-ethoxy-N-(4-methylphenyl)benzenesulfonamide (204 mg, 0.70 mmol, preparation described in example 1, step a)), was dissolved in DMF (5 mL). Methyl-2-bromopropionate (0.117 mL, 1.05 mmol) and potassium carbonate (193 mg, 1.40 mmol) were added. The mixture was heated overnight at 60° C. Solvents were evaporated. The crude residue was suspended in ethyl acetate (10 mL) and was washed with 1N HCl solution (7 mL) and with brine (7 mL). Organic phase was dried over MgSO4, fltrated and evaporated. The desired product, e.g. methyl 2-{[(4-ethoxyphenyl)sulfonyl]-4-methylanilino}propanoate (276 mg, quantitative crude yield) was isolated as a light yellow oil, in 94.3% purity by HPLC (MaxPlot detection between 230 and 400 nm).

후처리

  1. customSolvents were evaporated
  2. washwas washed with 1N HCl solution (7 mL) and with brine (7 mL)
  3. dry with materialOrganic phase was dried over MgSO4
  4. customevaporated

출처 및 근거

ORD 기록
ord-47c63fdbd517494bbc401ec578cd0e6f
출처 데이터셋
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07312358B2

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