Hydrochloric Acid → HCID 10157037, compound

HRID 584899Notes

Reaction equation

HRID 584899 reaction equation
[C:1]([N:9]([CH2:11][C:12]1[CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([CH3:31])[C:26]([O:28]CC)=[O:27])=[CH:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)[CH3:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C1COCC1.Cl>O.CO>[CH3:31][CH:25]([CH2:24][C:21]1[CH:20]=[CH:19][C:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([CH2:11][N:9]([CH3:10])[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:8])[CH:13]=2)=[CH:23][CH:22]=1)[C:26]([OH:28])=[O:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 10273326HCID 10273326, compound

Product 1

HCID 10157037HCID 10157037, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1.25 g (3 mmol) of ethyl 3-{3′-[(benzoyl-methylamino)methyl]biphenyl-4-yl}-2-methylpropionate, 3 ml of sodium hydroxide (10N), 32 ml of THF and 2 ml of methanol are introduced into a round-bottomed flask. The reaction medium is refluxed for 8 hours, poured into water, acidified to pH 4 with 1N hydrochloric acid and extracted with dichloromethane, and the organic phase is separated out after settling of the phases has taken place, dried over magnesium sulfate and evaporated. The residue obtained is purified by chromatography on a column of silica eluded with a mixture of heptane and ethyl acetate (60/40). 900 mg (90%) of 2-methyl-3-(3′-{[methyl-(1-phenylmethanoyl)-amino]methyl}biphenyl-4-yl)propionic acid, with a melting point of 60-61° C., are obtained.

Workup

  1. temperatureThe reaction medium is refluxed for 8 hours
  2. extractionextracted with dichloromethane
  3. customthe organic phase is separated out
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. additioneluded with a mixture of heptane and ethyl acetate (60/40)

Sources & evidence

ORD record
ord-8721ab39d20e476d92b66b795c87c062
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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