Acryloyl chloride → HCID 52939520, compound

HRID 1841934Notes

Reaction equation

HRID 1841934 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:37](Cl)(=[O:40])[CH:38]=[CH2:39]>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:37](=[O:40])[CH:38]=[CH2:39])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 56954946HCID 56954946, compound

Product 1

HCID 52939520HCID 52939520, compoundYield 8.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Amino-benzenesulfonylamino)-piperidine-1-carboxylic acid benzyl ester (1 g, 2.4 mmol) was dissolved in THF (10 ml). To this was added diisopropylethylamine (1.27 ml, 7.2 mmol) in one portion followed by the drop wise addition of acryloyl chloride (0.2 ml, 2.6 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours. The THF was removed under vacuum and the resulting crude material was purified by column chromatography (elution: 40% heptane, 60% ethyl acetate) to give the title compound (89 mg, 8% yield) as a white powder.

Workup

  1. customThe THF was removed under vacuum
  2. customthe resulting crude material was purified by column chromatography (elution: 40% heptane, 60% ethyl acetate)

Sources & evidence

ORD record
ord-beb5d3e301324ea7a22f04a2fe3d9635
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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