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

HRID 2199604노트

반응식

HRID 2199604 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-17ba6e78d1384395b673246df527d6c9
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359329B2

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