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Potassium Carbonate → Methyl 2-[(4-{3-[(2,4-difluorobenzyl)(heptyl)amino]-3-oxopropyl}phenoxy)methyl]benzoate

HRID 899877
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HRID 899877 반응식
[F:1][C:2]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:3]=1[CH2:4][N:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:6](=[O:16])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.[CH3:29][O:30][C:31](=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH2:38]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:1][C:2]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:3]=1[CH2:4][N:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:6](=[O:16])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:38][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[C:31]([O:30][CH3:29])=[O:40])=[CH:11][CH:10]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 69120490N-(2,4-difluorobenzyl)-N-heptyl-3-(4-hydroxyphenyl)propanamide

생성물 1

HCID 69120584Methyl 2-[(4-{3-[(2,4-difluorobenzyl)(heptyl)amino]-3-oxopropyl}phenoxy)methyl]benzoate수율 69.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

N-(2,4-difluorobenzyl)-N-heptyl-3-(4-hydroxyphenyl)propanamide (195 mg, 0.501 mmol), 2-bromomethylbenzoic acid methyl ester (120.4 mg, 0.526 mmol) and anhydrous potassium carbonate (103 mg, 0.751 mmol) were mixed in acetonitrile (15 ml). The mixture was heated to reflux overnight and then evaporated to dryness. Water and ethyl acetate were added and the two phases were separated. The organic phase was dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 2 g/6 ml) using heptane/DCM (50:50), then DCM and then MeOH/DCM (0.5:99.5) as eluant gave 187 mg desired product, yield 69.5%.

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customevaporated to dryness
  4. additionWater and ethyl acetate were added
  5. customthe two phases were separated
  6. dry with materialThe organic phase was dried (magnesium sulphate)
  7. customevaporated

출처 및 근거

ORD 기록
ord-8befef2263a140d08710caa4aaf54468
출처 데이터셋
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07355069B2

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