HCID 18958321, compound → HCID 18958311, compound

HRID 2379274Notes

Reaction equation

HRID 2379274 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:28]=[CH:27][C:17]([O:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[C:16]([N+:29]([O-])=O)[CH:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H][H]>[C].[Pd].C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:28]=[CH:27][C:17]([O:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:21])=[C:16]([NH2:29])[CH:15]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 18958321HCID 18958321, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18958311HCID 18958311, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

360 mg of 10% palladium-carbon were added to 15 ml of ethyl acetate solution of 3.61 g of t-butyl 4-[2-(4-chlorobenzenesulfonamido)ethyl]-2-nitrophenoxyacetate and stirred at one atmospheric pressure in the presence of hydrogen gas. The reaction mixture was filtered and concentrated under reduced pressure. The resulting residue was subjected to silica-gel column chromatography, whereupon 2.23 g (yield 66%) of t-butyl 4-[2-(4-chlorobenzenesulfonamido)ethyl]-2-aminophenoxyacetate were obtained from the fraction as eluted with hexane/ethyl acetate (2/1, v/v) as a yellow oily substance.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-afb8ad51dfe24dbcbfd50698b4cc859e
Source dataset
uspto-grants-1994_11
Patent number
US05360909

Reaction notes

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