Ethyl Acetate → 2-{[(4-{3-[(2,4-Difluorobenzyl)(heptyl)amino]-3-oxopropyl}phenyl)thio]methyl}benzoic acid

HRID 899881Notes

Reaction equation

HRID 899881 reaction equation
[F:1][C:2]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:3]=1[CH2:4][N:5]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:6](=[O:27])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][CH2:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([O:21]C)=[O:20])=[CH:11][CH:10]=1.[OH-].[K+].CCOC(C)=O>CCO>[F:1][C:2]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:3]=1[CH2:4][N:5]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:6](=[O:27])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([S:15][CH2:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([OH:21])=[O:20])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 69120239Methyl 2-{[(4-{3-[(2,4-difluorobenzyl)(heptyl)amino]-3-oxopropyl}phenyl)thio]methyl}benzoate

Product 1

HCID 104372812-{[(4-{3-[(2,4-Difluorobenzyl)(heptyl)amino]-3-oxopropyl}phenyl)thio]methyl}benzoic acidYield 94.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 2-{[(4-{3-[(2,4-difluorobenzyl)(heptyl)amino]-3-oxopropyl}phenyl)thio]methyl}benzoate (1.05 g, 1.89 mmol) was dissolved in EtOH (95%, 5 ml), potassium hydroxide (0.21 g, 3.77 mmol) was added. The reaction was performed in a single node microwave oven (7 min, 150° C.). Workup was by addition of EtOAc (5 ml) and washing with HCl (2×5 ml, 1M). The organic layer was dried (MgSO4) and the solvent was removed by evaporation to give 0.96 gram of 2-{[(4-{3-[(2,4-difluorobenzyl)(heptyl)amino]-3-oxopropyl}phenyl)thio]methyl}benzoic acid (yield 94.3%).

Workup

  1. customThe reaction was performed in a single node microwave oven
  2. custom(7 min, 150° C.)
  3. washwashing with HCl (2×5 ml, 1M)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-e0f28edfe43346358ac39c2e8b7ab5a0
Source dataset
uspto-grants-2008_04
Patent number
US07355069B2

Reaction notes

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