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

HRID 971320
ノート
印刷プレビュー

反応式

HRID 971320 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-47c63fdbd517494bbc401ec578cd0e6f
出典データセット
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07312358B2

反応ノート

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