1-Methylimidazole → 1-(4-Chlorobenzyl)-3-(4-toluenesulfonyloxy)methyl-3-methyl-2-oxo-cyclopentancarboxylic acid methyl ester

HRID 922735노트

반응식

HRID 922735 반응식
[CH3:1][O:2][C:3]([C:5]1([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:9][CH2:8][C:7]([CH2:11][OH:12])([CH3:10])[C:6]1=[O:13])=[O:4].C(N(CC)CC)C.CN1C=CN=C1.[C:35]1([CH3:45])[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1>C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]([C:5]1([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH2:9][CH2:8][C:7]([CH2:11][O:12][S:41]([C:38]2[CH:39]=[CH:40][C:35]([CH3:45])=[CH:36][CH:37]=2)(=[O:43])=[O:42])([CH3:10])[C:6]1=[O:13])=[O:4]

참가 물질

7

반응물 4

HCID 13901-MethylimidazoleHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 672540121-(4-Chlorobenzyl)-3-hydroxymethyl-3-methyl-2-oxocyclopentanecarboxylic acid methyl ester

생성물 1

HCID 867182551-(4-Chlorobenzyl)-3-(4-toluenesulfonyloxy)methyl-3-methyl-2-oxo-cyclopentancarboxylic acid methyl ester수율 75.8%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

In 95 ml of toluene, 4.756 g of Compound 2-1 obtained in Production Example 1 was dissolved. To the solution thus obtained, 3.12 ml of triethylamine and 1.76 ml of N-methylimidazole were added, and 3.38 g of 4-toluenesulfonyl chloride was added. The resulting mixture was stirred at room temperature for 100 minutes. After the reaction, water was added to the reaction solution thus obtained, and the organic layer was separated from the suspension. Thereafter, the aqueous layer was extracted with toluene and then blended with the organic layer previously obtained. The resultant organic layer thus obtained was washed with an aqueous solution of 1 mol/l hydrochloric acid and saturated brine and then dried over anhydrous sodium sulfate. The solvent was distilled away, and the residue was then purified by silica gel column chromatography to obtain 5.397 g of Compound 3-1-2.

후처리

  1. dissolutionwas dissolved
  2. customTo the solution thus obtained
  3. additionwas added to the reaction solution
  4. customthus obtained
  5. customthe organic layer was separated from the suspension
  6. extractionThereafter, the aqueous layer was extracted with toluene
  7. custompreviously obtained
  8. customThe resultant organic layer thus obtained
  9. washwas washed with an aqueous solution of 1 mol/l hydrochloric acid and saturated brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationThe solvent was distilled away
  12. customthe residue was then purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-b36ebe72e0254bafb75aae5438d2d478
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278966B2

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