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

HRID 899877
Notes
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Reaction equation

HRID 899877 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-8befef2263a140d08710caa4aaf54468
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07355069B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes