Benzoate → Benzoic Acid

HRID 732702Notes

Reaction equation

HRID 732702 reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(O)C>[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 242BenzoateHCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 214 mg portion of ethyl 4-{[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}amino)benzoate was dissolved in 5.0 ml of ethanol, mixed with 1.0 ml of 1 M sodium hydroxide aqueous solution and stirred overnight at room temperature. The reaction solution was poured into 1 M hydrochloric acid, and the thus formed precipitate was collected by filtration. The thus obtained solid matter was purified by a silica gel column chromatography (chloroform-methanol) to obtain 131 mg of 4-{[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}amino)benzoic acid as a colorless amorphous substance.

Workup

  1. filtrationthe thus formed precipitate was collected by filtration
  2. customThe thus obtained solid matter was purified by a silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-feec9cb05b924c8389585ee579b3a503
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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