Diisopropylcarbodiimide → N-[2-(3-methoxyphenyl)ethyl]-2-[4-(phenylmethoxy)phenyl]acetamide

HRID 1180145

반응식

HRID 1180145 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N=C=NC(C)C)(C)C.[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH2:36][CH2:37][NH2:38])[CH:33]=[CH:34][CH:35]=1>CN(C)C=O>[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH2:36][CH2:37][NH:38][C:16](=[O:18])[CH2:15][C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:14][CH:13]=2)[CH:33]=[CH:34][CH:35]=1

참가 물질

5

반응물 3

HCID 12734DiisopropylcarbodiimideHCID 748663-MethoxyphenethylamineHCID 810334-Benzyloxyphenylacetic acid

생성물 1

HCID 12950733N-[2-(3-methoxyphenyl)ethyl]-2-[4-(phenylmethoxy)phenyl]acetamide수율 76.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-benzyloxyphenylacetic acid (4.85 g 20 mmol) in dimethylformamide (30 mL) under nitrogen was added 1,3-diisopropylcarbodiimide. After 2 hours, to the solution was added 2-(3-methoxyphenyl)ethylamine (3.02 g, 20 mmol) and stirred at room temperature for 20 hours. The reaction was quenched with a saturated sodium carbonate solution and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was then purified by chromatography (SiO2, 30-70% ethyl acetate/hexane) to provide the title compound (5.74 g, 76% yield): 1H NMR (CDCl3) 7.38 (m, 5H), 7.14 (t, 1H), 7.07 (d, 2H), 6.91 (d, 2H), 6.74 (dd, 1H), 6.62 (m, 2H), 5.37 (br, 1H), 5.06 (s, 2H), 3.77 (s, 3H), 3.47 (s, 2H), 3.44 (t, 2H), 2.70 (t, 2H); ES-MS (m/z) 376 [M+H]+.

후처리

  1. customThe reaction was quenched with a saturated sodium carbonate solution
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was then purified by chromatography (SiO2, 30-70% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-24d1ddc51f534fed8e52fd1962e33440
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279489B2

연결된 노트

불러오는 중…