Benzenesulfonyl chloride → Ethyl 3-benzenesulfonamidopropanoate

HRID 2384069ノート

反応式

HRID 2384069 の反応式
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]([O:13][C:14](=[O:18])[CH2:15][CH2:16][NH2:17])[CH3:12].C(OCC)(=O)C>N1C=CC=CC=1>[CH2:11]([O:13][C:14](=[O:18])[CH2:15][CH2:16][NH:17][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])[CH3:12]

参加物

5

反応物 3

HCID 7369Benzenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 419889Ethyl 3-aminopropanoate

生成物 1

HCID 3795547Ethyl 3-benzenesulfonamidopropanoate

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a solution of benzenesulfonyl chloride (500 mg, 2.83 mmol) in pyridine (10 mL) is added 3-amino-propionic acid ethyl ester (672 mg, 8.49 mmol) and the mixture is stirred at room temperature for 18 hours. The mixture is poured into ethyl acetate and is washed with aqueous 1M HCl and brine. The organic phase is dried over magnesium sulfate and the solvent is removed under reduced pressure. The residue is purified by column chromatography using a gradient of 10-50% heptane/EtOAc to afford 3-benzenesulfonylaminopropionic acid ethyl ester. MS 258.3 (M+1); 1H-NMR (400 MHz, CDCl3); δ ppm 1.24 (t, 3H), 2.53 (t, 2H), 3.21 (q, 2H), 5.22 (m, 1H), 7.51-7.61 (m, 3H), 7.87 (d, J=7.20 Hz, 2H).

後処理

  1. washis washed with aqueous 1M HCl and brine
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customthe solvent is removed under reduced pressure
  4. customThe residue is purified by column chromatography

出典と根拠

ORDレコード
ord-aa91a0ae05ba456dbee4bec79c5bea52
出典データセット
uspto-grants-2012_09
特許番号
US08263629B2

反応ノート

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