HCID 18950712, compound → HCID 9934618, compound

HRID 1492514Notes

Reaction equation

HRID 1492514 reaction equation
C(OC([N:11]([CH2:22][CH:23]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:32][CH:31]=1)[C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[S:12]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])=O)C1C=CC=CC=1>C(O)C.[C].[Pd]>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([S:12]([NH:11][CH2:22][CH:23]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:32][CH:31]=2)[C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)(=[O:13])=[O:14])=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 18950712HCID 18950712, compound

Product 1

HCID 9934618HCID 9934618, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In 10 ml of ethanol were suspended 0.23 g of the thus obtained ethyl 4-{2-[N-benzyloxycarbonyl-N-(4-chlorobenzenesulfonyl)amino]-1-(3pyridyl)ethyl}phenyloxyacetate and 0.14 g of 10% palladium-carbon. The thus prepared suspension was subjected to 14 hours of catalytic reduction reaction at ambient temperature and pressure. The resulting reaction mixture was filtered to collect filtrate, and the solvent in the filtrate was removed by distillation under a reduced pressure. Thereafter, the resulting residue was applied to silica gel preparative TLC and developed twice with methanol-methylene chloride (5:95 v/v) to obtain 0.12 g of ethyl 4-[2-(4-chlorobenzenesulfonamido)-1-(3-pyridyl)ethyl]phenyloxyacetate from the band at an Rf value of from 0.65 to 0.43.

Workup

  1. customThe thus prepared suspension was subjected to 14 hours of catalytic reduction reaction at ambient temperature
  2. customThe resulting reaction mixture
  3. filtrationwas filtered
  4. customto collect filtrate
  5. customthe solvent in the filtrate was removed by distillation under a reduced pressure

Sources & evidence

ORD record
ord-0cdfbf8761344a5abc9b8cfa3e9c28a9
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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