Pyridine → (5-{1-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-hydroxy-ethylcarbamoyl}-pentyl)-carbamic acid 17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

HRID 1893032

반응식

HRID 1893032 반응식
[CH3:1][CH:2]([CH:9]1[C:25]2([CH3:26])[CH:12]([CH:13]3[CH:22]([CH2:23][CH2:24]2)[C:21]2([CH3:27])[C:16]([CH2:17][CH:18]([O:28][C:29](=[O:44])[NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36](=[O:43])[NH:37][CH:38]([CH2:41][OH:42])[CH2:39][OH:40])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].CN([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50]N=1)C.[C:54](Cl)(C1C=CC=CC=1)([C:63]1[CH:70]=[CH:69][C:66]([O:67][CH3:68])=[CH:65][CH:64]=1)[C:55]1[CH:62]=[CH:61][C:58]([O:59][CH3:60])=[CH:57][CH:56]=1.N1C=CC=C[CH:79]=1>>[CH3:1][CH:2]([CH:9]1[C:25]2([CH3:26])[CH:12]([CH:13]3[CH:22]([CH2:23][CH2:24]2)[C:21]2([CH3:27])[C:16]([CH2:17][CH:18]([O:28][C:29](=[O:44])[NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36](=[O:43])[NH:37][CH:38]([CH:39]([C:50]4[CH:79]=[CH:48][CH:53]=[CH:52][CH:51]=4)[O:40][CH:54]([C:55]4[CH:62]=[CH:61][C:58]([O:59][CH3:60])=[CH:57][CH:56]=4)[C:63]4[CH:64]=[CH:65][C:66]([O:67][CH3:68])=[CH:69][CH:70]=4)[CH2:41][OH:42])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:7])[CH3:8]

참가 물질

5

반응물 4

HCID 1049Pyridine2회HCID 218852-DimethylaminopyridineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 68636631[5-(2-Hydroxy-1-hydroxymethyl-ethylcarbamoyl)-pentyl]-carbamic acid 17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

생성물 1

HCID 131728218(5-{1-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-hydroxy-ethylcarbamoyl}-pentyl)-carbamic acid 17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

실험 절차

Diol 52 (5.6 g, 9.1 mmol) was co-evaporated with anhydrous pyridine three times and then dissolved in pyridine (10 mL). To this solution dimethylamino pyridine (0.110 g, 0.91 mmol) and DMT-Cl (3.23 g, 9.53 mmol, 1.05 equiv.) were added at room temperature. The reaction mixture was stirred at room temperature for 16 h. Due to the presence of two primary hydroxyl groups, the reaction never went to completion. The solution was dried under reduced pressure and co-evaporated with toluene to remove residual pyridine. To the residue was suspended in ethyl acetate (200 mL) and washed with saturated bicarbonate solution, brine and water. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated. The crude product was obtained after removal of the solvent. Upon purification over silica gel using 2% MeOH/DCM compound 53 (0.680 g, 10%) was obtained as white foamy solid.

후처리

  1. customDue to the presence of two primary hydroxyl groups, the reaction
  2. dry with materialThe solution was dried under reduced pressure and co-evaporated with toluene
  3. customto remove residual pyridine
  4. washwashed with saturated bicarbonate solution, brine and water
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated

출처 및 근거

ORD 기록
ord-ade9804d3e21486789161de04c317706
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507661B2

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