Hydrochloric Acid → 4-Methoxy-3-(3-m-tolyl-propyl)-benzoic acid methyl ester

HRID 1475717Notes

Reaction equation

HRID 1475717 reaction equation
COC(C1(N[C:13](=[O:34])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([CH:22](O)[CH2:23][CH:24](O)[C:25]3[CH:26]=[C:27]([CH3:31])[CH:28]=[CH:29][CH:30]=3)[CH:15]=2)CCCCCC1)=O.Cl.[H][H].[CH2:38]([OH:40])C>[Pd]>[CH3:38][O:40][C:13](=[O:34])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[C:27]([CH3:31])[CH:28]=[CH:29][CH:30]=2)[CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 671695371-[3-(1,3-Dihydroxy-3-m-tolyl-propyl)-4-methoxy-benzoylamino]-cycloheptanecarboxylic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 670764524-Methoxy-3-(3-m-tolyl-propyl)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The compound of step 1 (140 mg, 0.424 mmol) was dissolved in ethanol (10 ml), 12 N hydrochloric acid (0.2 ml) and palladium on charcoal (10%) was added, and the mixture was hydrogenated at a hydrogen pressure of 6 bar at room temperature overnight. After filtration and evaporation, the residue was purified by silica gel chromatography (HEP/EA gradient) to give 80 mg of the title compound.

Workup

  1. filtrationAfter filtration and evaporation
  2. customthe residue was purified by silica gel chromatography (HEP/EA gradient)

Sources & evidence

ORD record
ord-77554662cf9c4f04a0bad5c3908d901d
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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