p-Toluenesulfonic acid → 6-chloro-N-cyclopentyl-N-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]pyridine-3-sulfonamide

HRID 2199604ノート

反応式

HRID 2199604 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:12][CH:13]([OH:16])[CH2:14][OH:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1.CO[C:24](OC)([CH3:26])[CH3:25].CC1C=CC(S(O)(=O)=O)=CC=1>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:12][CH:13]2[CH2:14][O:15][C:24]([CH3:26])([CH3:25])[O:16]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 866599586-chloro-N-cyclopentyl-N-(2,3-dihydroxypropyl)pyridine-3-sulfonamide

生成物 1

HCID 866599596-chloro-N-cyclopentyl-N-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]pyridine-3-sulfonamide収率 99%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 0.83 g (2.48 mmol) of 6-chloro-N-cyclopentyl-N-(2,3-dihydroxypropyl)pyridine-3-sulfonamide, 0.67 mL (5.45 mmol) of 2,2-dimethoxypropane and 47 mg of pTsOH in 5 mL of DMF is stirred for 3 hours at room temperature. The medium is taken up in 100 mL of EtOAc, washed with 50 mL of saturated NaHCO3 solution and 50 mL of water, and then dried over Na2SO4, filtered and concentrated under reduced pressure. 0.92 g 6-chloro-N-cyclopentyl-N-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]pyridine-3-sulfonamide is obtained in the form of a brown oil, which is used without further purification in the following step.

後処理

  1. washwashed with 50 mL of saturated NaHCO3 solution and 50 mL of water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-17ba6e78d1384395b673246df527d6c9
出典データセット
uspto-grants-2016_06
特許番号
US09359329B2

反応ノート

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