Hydrochloric Acid → 2-(4-(((Benzyloxy)carbonyl)amino)phenoxy)acetic acid

HRID 1780285Notes

Reaction equation

HRID 1780285 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]([NH:13][C:14]1[CH:26]=[CH:25][C:17]([O:18][CH2:19][C:20]([O:22]CC)=[O:21])=[CH:16][CH:15]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>CO>[CH2:3]([O:10][C:11]([NH:13][C:14]1[CH:15]=[CH:16][C:17]([O:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:25][CH:26]=1)=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19049900HCID 19049900, compound

Product 1

HCID 190498322-(4-(((Benzyloxy)carbonyl)amino)phenoxy)acetic acidYield 91.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.67 ml (1.67 mmol) of a 1N aqueous solution of sodium hydroxide were added, whilst ice-cooling, to a solution of 500 mg (1.52 mmol) of ethyl 4-(benzyloxycarbonylamino)phenoxyacetate (prepared as described in Preparation 14) in 10 ml of methanol, and the mixture was stirred at room temperature for 1 hour. At the end of this time, the reaction mixture was neutralized by the addition of 1N aqueous hydrochloric acid, and the solvent was removed by distillation under reduced pressure. The residue was diluted with ethyl acetate, and the resulting organic solution was washed with a 5% w/v aqueous solution of citric acid and with a saturated aqueous solution of sodium chloride, in that order. The reaction mixture was then dried over sodium sulfate, and the organic solvent was removed by distillation under reduced pressure. The concentrate was triturated with diethyl ether, to give 417 mg of the title compound as colorless crystals, melting at 152°-154° C.

Workup

  1. customthe solvent was removed by distillation under reduced pressure
  2. additionThe residue was diluted with ethyl acetate
  3. washthe resulting organic solution was washed with a 5% w/v aqueous solution of citric acid and with a saturated aqueous solution of sodium chloride, in that order
  4. dry with materialThe reaction mixture was then dried over sodium sulfate
  5. customthe organic solvent was removed by distillation under reduced pressure
  6. customThe concentrate was triturated with diethyl ether

Sources & evidence

ORD record
ord-a29fadec1f274d2baab7c3b9884a2fbd
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

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