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1,2-Dichloroethane → 4-[4-(1-Oxo-but-2-ynylamino)-benzenesulfonyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1841918
Notes
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Reaction equation

HRID 1841918 reaction equation
[C:1]([OH:6])(=O)[C:2]#[C:3][CH3:4].N1C=CC=CC=1.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([S:26]([C:29]2[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(Cl)CCl>C1COCC1.CC(N(C)C)=O.C(OCC)(=O)C>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([S:26]([C:29]2[CH:30]=[CH:31][C:32]([NH:35][C:1](=[O:6])[C:2]#[C:3][CH3:4])=[CH:33][CH:34]=2)(=[O:28])=[O:27])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 1049PyridineHCID 685352-Butynoic acidHCID 10617209tert-Butyl 4-(4-aminophenylsulfonyl)piperazine-1-carboxylate

Product 1

HCID 569547204-[4-(1-Oxo-but-2-ynylamino)-benzenesulfonyl]-piperazine-1-carboxylic acid tert-butyl esterYield 20.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent
HCID 69293768tetrahydrofuran N,N-dimethylacetamideSolvent

Procedure

But-2-ynoic acid (0.19 g, 2.36 mmol) followed by pyridine (0.6 ml), were added sequentially portion wise to a stirred solution of 4-(4-amino-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester (0.2 g, 0.59 mmol) in THF/DMA (3:2, 5 ml) at room temperature. To this mixture was added EDC (0.6 g, 3.1 mmol) in one portion and the mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour. After this time the mixture was diluted with ethyl acetate (50 ml) and washed with water (100 ml), saturated NaHCO3 (100 ml) and HCl (100 ml, 2M). The organic layer was separated, dried (MgSO4), filtered and concentrated under vacuum and the resulting residue was purified by flash column chromatography (elution, 20% ethyl acetate, 80% DCM) to give the title compound (0.05 g, 19% yield) as a white solid. Tr=4.12 min, m/z (ES+) (M+Na)+ 430.

Workup

  1. washwashed with water (100 ml), saturated NaHCO3 (100 ml) and HCl (100 ml, 2M)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customthe resulting residue was purified by flash column chromatography (elution, 20% ethyl acetate, 80% DCM)

Sources & evidence

ORD record
ord-c8e797c64b3f47c9883cc0d88d728f0a
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946197B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes