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Nitrogen → HCID 57719158, 화합물

HRID 1985241
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HRID 1985241 반응식
C([O:3][C:4]([C:6]1([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])C.[CH3:18][C:19]1[CH:47]=[CH:46][C:22]([CH2:23][N:24]2[CH2:28][CH:27]([CH2:29][CH2:30]OS(C3C=CC(C)=CC=3)(=O)=O)[N:26]([CH2:42][CH2:43][CH3:44])[C:25]2=[O:45])=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+].N#N.[OH-].[Na+]>C(O)C>[CH3:18][C:19]1[CH:47]=[CH:46][C:22]([CH2:23][N:24]2[CH2:28][CH:27]([CH2:29][CH2:30][O:17][C:14]3[CH:13]=[CH:12][C:11]([C:6]4([C:4]([OH:3])=[O:5])[CH2:7][CH2:8][CH2:9][CH2:10]4)=[CH:16][CH:15]=3)[N:26]([CH2:42][CH2:43][CH3:44])[C:25]2=[O:45])=[CH:21][CH:20]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 57718928HCID 57718928, 화합물HCID 57719317HCID 57719317, 화합물

생성물 1

HCID 57719158HCID 57719158, 화합물수율 40%

시약·촉매·용매 1

HCID 702
Ethanol
용매

실험 절차

A mixture of 1-(4-hydroxy-phenyl)-cyclopentanecarboxylic acid ethyl ester (0.042 g, 0.179 mmol), toluene-4-sulfonic acid 2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-imidazolidin-4-yl]-ethyl ester (0.085 g, 0.197 mmol) and 325 mesh K2CO3 (0.050 g, 0.362 mmol) in ethanol (5 mL) was heated at ref lux for under N2 for 16 h. The reaction was then treated with aqueous 5 N NaOH (0.5 mL) and heated to reflux 1.5 h. The reaction mixture was cooled, the solvent removed in vacuo. The resultant residue was acidified with aqueous 1 N HCl (10 mL) and extracted with Et2O. The organic layer was dried (MgSO4) and the solvent removed in vacuo to afford 0.058 g crude acid that was purified by preparative HPLC to afford 0.033 g (40%) 1-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-imidazolidin-4-yl]-ethoxy}-phenyl)-cyclopentanecarboxylic acid. MS (ES+) Calc'd for C28H37N2O4 (M+1) 465. Found m/z 465 (100%). 1H NMR.

후처리

  1. temperatureheated
  2. temperatureto reflux 1.5 h
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent removed in vacuo
  5. extractionextracted with Et2O
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customthe solvent removed in vacuo
  8. customto afford 0.058 g crude acid that
  9. customwas purified by preparative HPLC

출처 및 근거

ORD 기록
ord-47e13ea165ca4f45ae068b65d00b2349
출처 데이터셋
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07544812B2

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