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

HRID 899894ノート

反応式

HRID 899894 の反応式
[F:1][C:2]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:3]=1[CH2:4][N:5]([CH2:17][CH2:18][CH3:19])[C:6](=[O:16])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.[CH3:25][O:26][C:27](=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH2:34]Br.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[F:1][C:2]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:3]=1[CH2:4][N:5]([CH2:17][CH2:18][CH3:19])[C:6](=[O:16])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:34][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[C:27]([O:26][CH3:25])=[O:36])=[CH:11][CH:10]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 69120491N-(2,4-difluorobenzyl)-3-(4-hydroxyphenyl)-N-propylpropanamide

生成物 1

HCID 69179959Methyl 2-[(4-{3-[(2,4-difluorobenzyl)(propyl)amino]-3-oxopropyl}phenoxy)methyl]benzoate収率 44%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

N-(2,4-Difluorobenzyl)-3-(4-hydroxyphenyl)-N-propylpropanamide (290 mg, 0.87 mmol) was dissolved in acetonitrile (10 ml). 2-Bromomethyl-benzoic acid methyl ester (209 mg, 0.913 mmol) was added followed by potassium carbonate, anhydrous (180 mg, 1.305 mmol). The mixture was heated to reflux overnight and then evaporated to dry. Water and ethyl acetate were added and two phases were separated. The organic phase was dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE®SI, 20 g/70 ml) using DCM and then MeOH/DCM (1:99) as eluant gave 184 mg the desired product, yield 44%.

後処理

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

出典と根拠

ORDレコード
ord-b117dbd55e164740be3ee074969ee399
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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