4-[4-(1-Oxo-but-2-ynylamino)-benzenesulfonyl]-piperazine-1-carboxylic acid tert-butyl ester → 4-(4-(Z)-But-2-enoylamino-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1841919Notes

Reaction equation

HRID 1841919 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:28])[C:25]#[C:26][CH3:27])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([S:14]([C:17]2[CH:18]=[CH:19][C:20]([NH:23][C:24](=[O:28])/[CH:25]=[CH:26]\[CH3:27])=[CH:21][CH:22]=2)(=[O:15])=[O:16])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 569547204-[4-(1-Oxo-but-2-ynylamino)-benzenesulfonyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 569545024-(4-(Z)-But-2-enoylamino-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl esterYield 44.4%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent

Procedure

Lindlar's catalyst (0.005 g, 0.001 mmol) was added in one portion to a stirred solution of 4-[4-(1-oxo-but-2-ynylamino)-benzenesulfonyl]-piperazine-1-carboxylic acid tert-butyl ester (0.05 g, 0.11 mmol) in methanol (5 ml) at room temperature, the resulting mixture was then stirred at room temperature under a hydrogen atmosphere for 2 hours. After this time, the reaction mixture was filtered through celite and concentrated under vacuum to give the title compound (0.02 g, 40% yield) as a white solid.

Workup

  1. filtrationAfter this time, the reaction mixture was filtered through celite
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-918e9c28892e4434b87a8eb2dbabd953
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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