HCID 14722309, compound → HCID 10620577, compound

HRID 1031680Notes

Reaction equation

HRID 1031680 reaction equation
C([O:8][C:9]1[CH:22]=[C:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[C:20]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:19][C:10]=1[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:12])C1C=CC=CC=1>C(O)C.[C].[Pd]>[OH:8][C:9]1[CH:22]=[C:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[C:20]([O:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:19][C:10]=1[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:12]

Participants

4

Reactant 1

HCID 14722309HCID 14722309, compound

Product 1

HCID 10620577HCID 10620577, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In 50 ml of ethanol was dissolved 4.83 g of ethyl 2-(2-benzyloxy-4-methylsulfonylamino-5-phenoxybenzoyl)acetate. Thereto was added 200 mg of 5% palladium-carbon. The mixture was subjected to hydrogenation for 1 hour at 40° C. at atmospheric pressure. After the completion of the reaction, the catalyst was removed by filtration. The filtrate was subjected to distillation under reduced pressure to remove the solvent. The residue was mixed with diisopropyl ether. The resulting crystal was collected by filtration and recrystallized from a mixed solvent of ethyl acetate and diisopropyl ether to obtain 3.46 g (yield: 88%) of ethyl 2-(2-hydroxy-4-methylsulfonylamino-5-phenoxybenzoyl)acetate having a melting point of 111.5°-112.5° C.

Workup

  1. customAfter the completion of the reaction
  2. customthe catalyst was removed by filtration
  3. distillationThe filtrate was subjected to distillation under reduced pressure
  4. customto remove the solvent
  5. additionThe residue was mixed with diisopropyl ether
  6. filtrationThe resulting crystal was collected by filtration
  7. customrecrystallized from a mixed solvent of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-1eed135637b34bfcba7753e0594d2d0b
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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