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

HRID 2112029ノート

反応式

HRID 2112029 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-af8ff9fcbf7b4f3da9f3456e11896101
出典データセット
uspto-grants-2009_04
特許番号
US07521461B2

反応ノート

読み込み中…