3-(4-Hydroxyphenyl)propionic acid → N-[2-(2-ethoxyphenyl)ethyl]-3-(4-hydroxyphenyl)propanamide

HRID 2112029노트

반응식

HRID 2112029 반응식
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][NH2:12])[CH3:2].[OH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22](O)=[O:23])=[CH:16][CH:15]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O.CCOC(C)=O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][NH:12][C:22](=[O:23])[CH2:21][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([OH:13])=[CH:15][CH:16]=1)[CH3:2]

참가 물질

7

반응물 4

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 81531DiisopropylethylamineHCID 1423622-EthoxyphenethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

생성물 1

HCID 68873053N-[2-(2-ethoxyphenyl)ethyl]-3-(4-hydroxyphenyl)propanamide수율 104.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

2-(2-Ethoxyphenyl)ethanamine (0.55 g, 3.33 mmol) and 3-(4-hydroxyphenyl)propanoic acid (0.50 g, 3.00 mmol) was dissolved in dimethyl formamide (5 ml) and cooled to 0° C. N-[(1H-1,2,3-benzotriazol-1-yloxy)(dimethylamino)methylene]-N-methylmethanaminium tetrafluoroborate (1.18 g, 3.66 mmol) and diisopropylethylamine (0.90 g, 7.0 mmol) were added and the solution was warmed to room temperature and stirred overnight. EtOAc (15 ml) was added and the organic phase was washed with two portions of sodium hydrogencarbonate (aq, 10 ml). The organic phase was dried (MgSO4) and EtOAc was removed by evaporation to give 0.98 gram of N-[2-(2-ethoxyphenyl)ethyl]-3-(4-hydroxyphenyl)propanamide (yield 93.9%).

후처리

  1. temperaturethe solution was warmed to room temperature
  2. washthe organic phase was washed with two portions of sodium hydrogencarbonate (aq, 10 ml)
  3. dry with materialThe organic phase was dried (MgSO4) and EtOAc
  4. customwas removed by evaporation

출처 및 근거

ORD 기록
ord-af8ff9fcbf7b4f3da9f3456e11896101
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07521461B2

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