Acryloyl chloride → HCID 67195292, compound

HRID 1841961Notes

Reaction equation

HRID 1841961 reaction equation
C(N(C(C)C)CC)(C)C.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].[C:33](Cl)(=[O:36])[CH:34]=[CH2:35]>C1COCC1>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:36])[CH:34]=[CH2:35])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 57516500HCID 57516500, compound

Product 1

HCID 67195292HCID 67195292, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylethylamine (0.09 ml, 0.5 mmol) was added in one portion to a stirred solution of 4-(4-Amino-benzenesulfonyl)-piperidine-1-carboxylic acid tert-butyl ester (0.11 g, 0.33 mmol) in THF (3 ml) at room temperature. To this mixture was added acryloyl chloride (0.03 ml, 0.5 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 (0.02 g, 17% 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-5378c85dd9fb480e9700e26eb6d8011a
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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