Acryloyl chloride → HCID 67195330, compound

HRID 1841958Notes

Reaction equation

HRID 1841958 reaction equation
C(N(C(C)C)CC)(C)C.[CH3:10][N:11]([CH3:30])[C:12]([CH:14]1[CH2:19][CH2:18][N:17]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH2:16][CH2:15]1)=[O:13].[C:31](Cl)(=[O:34])[CH:32]=[CH2:33]>C1COCC1>[CH3:10][N:11]([CH3:30])[C:12]([CH:14]1[CH2:15][CH2:16][N:17]([S:20]([C:23]2[CH:24]=[CH:25][C:26]([NH:29][C:31](=[O:34])[CH:32]=[CH2:33])=[CH:27][CH:28]=2)(=[O:22])=[O:21])[CH2:18][CH2:19]1)=[O:13]

Participants

5

Reactant 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 61113174HCID 61113174, compound

Product 1

HCID 67195330HCID 67195330, compoundYield 16.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylethylamine (0.1 ml, 0.7 mmol) was added in one portion to a stirred solution of 1-(4-amino-benzenesulfonyl)-piperidine-4-carboxylic acid dimethylamide (0.15 g, 0.49 mmol) in THF (3 ml) at room temperature. To this mixture was added acryloyl chloride (0.05 ml, 0.58 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 concentrated under vacuum and the resulting residue was purified by column chromatography (elution: 40% heptane, 60% ethyl acetate) to give the title compound (0.03 g, 15% yield) as a white solid.

Workup

  1. concentrationAfter this time, the mixture was concentrated under vacuum
  2. customthe resulting residue was purified by column chromatography (elution: 40% heptane, 60% ethyl acetate)

Sources & evidence

ORD record
ord-26bd0532a5d04c50ab7f22a63faf7e0f
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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