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

HRID 899893노트

반응식

HRID 899893 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%.

후처리

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

출처 및 근거

ORD 기록
ord-3ce818fdfd1441a98695c0d1f53b0c77
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07355069B2

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