Hydrochloric Acid → HCID 21958048, compound

HRID 2299208Notes

Reaction equation

HRID 2299208 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([O:14][C:15]([NH:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][C:19]=1[Cl:28])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.Cl>CS(C)=O>[CH2:7]([O:14][C:15]([NH:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([OH:24])=[O:23])=[CH:20][C:19]=1[Cl:28])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21958042HCID 21958042, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21958048HCID 21958048, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium t-butoxide (24.7 g) was dissolved in dimethylsulfoxide (221 ml) and admixed with methyl 4-benzyloxycarbonylamino-3-chlorobenzoate (4.52 g) and the mixture was stirred at room temperature for 25 minutes. The reaction mixture was poured into water (200 ml), which was then acidified with 1N hydrochloric acid (225 ml) and then extracted with ethyl acetate. The ethyl acetate layer was washed successively with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate/hexane=2:5). A desired fraction was concentrated under reduced pressure to obtain 4-benzyloxycarbonylamino-3-chlorobenzoic acid (2.47 g) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed successively with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (ethyl acetate/hexane=2:5)
  6. concentrationA desired fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4694f3c9470744059232718b8b1edbaf
Source dataset
uspto-grants-2002_12
Patent number
US06495604B1

Reaction notes

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