3-(4-Hydroxyphenyl)propionic acid → N-(2,4-difluorobenzyl)-3-(4-hydroxyphenyl)-N-propylpropanamide

HRID 899893ノート

反応式

HRID 899893 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[F:13][C:14]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:15]=1[CH2:16][NH:17][CH2:18][CH2:19][CH3:20].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.C(=O)([O-])O.[Na+]>CN(C=O)C>[F:13][C:14]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:15]=1[CH2:16][N:17]([CH2:18][CH2:19][CH3:20])[C:10](=[O:12])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1

参加物

7

反応物 5

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 24690356[(2,4-Difluorophenyl)methyl](propyl)amine

生成物 1

HCID 69120491N-(2,4-difluorobenzyl)-3-(4-hydroxyphenyl)-N-propylpropanamide収率 68.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3-(4-Hydroxyphenyl)propionic acid (245 mg, 1.474 mmol) in DMF (5 ml) was cooled in an ice-bath. N-(2,4-Difluorobenzyl)-N-propylamine (300.4 mg, 1.622 mmol) was added and then TBTU (521 mg, 1.622 mmol) followed by DIPEA (400 mg, 3.096 mmol). The mixture was stirred at room temperature overnight. Sodium hydrogencarbonate aqueous solution (sat.) was added. The mixture was extracted with ethyl acetate (×2). The extracts were combined and dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 5 g/25 ml) using DCM/heptane (50:50), DCM and then MeOH/DCM (1:99, then 2:98) as eluant gave 336 mg the desired product, yield 68%.

後処理

  1. extractionThe mixture was extracted with ethyl acetate (×2)
  2. dry with materialdried (magnesium sulphate)
  3. customevaporated

出典と根拠

ORDレコード
ord-3ce818fdfd1441a98695c0d1f53b0c77
出典データセット
uspto-grants-2008_04
特許番号
US07355069B2

反応ノート

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