Imidazole → HCID 15228564, compound

HRID 1609483Notes

Reaction equation

HRID 1609483 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[C:14]1([C:20]([NH:33][C@@H:34]([CH2:37][C:38]2[N:42]([C:43]([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH:41]=[N:40][CH:39]=2)[CH2:35][OH:36])([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C=O)C>[Si:6]([O:36][CH2:35][C@@H:34]([NH:33][C:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:37][C:38]1[N:42]([C:43]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:41]=[N:40][CH:39]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 15228563HCID 15228563, compound

Product 1

HCID 15228564HCID 15228564, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (12.269 g, 0.180 mol) and tert-butyldimethylsilyl chloride (TBDMSCl) (20.37 g, 0.135 mol) were added to a solution of the compound (XXI) (56.390 g, 0.0901 mol) in dry DMF (560 ml) under ice cooling, and the mixture was stirred at room temperature for 3.5 hours. The reaction mixture was poured into water, extracted with Et2O, washed with water and a saturated NaCl aqueous solution, then dried over Na2SO4, and concentrated to obtain a light-yellow foamy material (67.602 g). This crude product was purified by silica gel column chromatography (hexane/acetone=5/1) to obtain the objective compound (XX) (58.770 g; yield: 88.1%) as a white foamy material.

Workup

  1. extractionextracted with Et2O
  2. washwashed with water
  3. dry with materiala saturated NaCl aqueous solution, then dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2526961bef8f4b44abc39114126f37a6
Source dataset
uspto-grants-1995_03
Patent number
US05401736

Reaction notes

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