Benzenesulfonyl chloride → Ethyl 3-benzenesulfonamidopropanoate

HRID 1469647노트

반응식

HRID 1469647 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 3795547Ethyl 3-benzenesulfonamidopropanoate

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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=7.20Hz, 2H).

후처리

  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

출처 및 근거

ORD 기록
ord-edfce6f0e6c94529a7df066f82b40972
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006249B2

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