Imidazole → HCID 68466455, compound

HRID 895323Notes

Reaction equation

HRID 895323 reaction equation
C([C@@:9]1([N:40]2[C:49]3[N:48]=[CH:47][N:46]=[C:44]([NH2:45])[C:43]=3[N:42]=[C:41]2[Br:50])[O:39][C@H:13]([CH2:14][O:15][C:16]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[C@@H:11]([OH:12])[CH2:10]1)(=O)C1C=CC=CC=1.N1[CH:55]=[CH:54]N=C1.[C:56]([Si:60](Cl)([CH3:62])[CH3:61])([CH3:59])([CH3:58])[CH3:57].CN([CH:67]=[O:68])C>>[C:67]([NH:45][C:44]1[C:43]2[N:42]=[C:41]([Br:50])[N:40]([C:49]=2[N:48]=[CH:47][N:46]=1)[C@@H:9]1[O:39][C@H:13]([CH2:14][O:15][C:16]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)[C@@H:11]([O:12][Si:60]([C:56]([CH3:59])([CH3:58])[CH3:57])([CH3:62])[CH3:61])[CH2:10]1)(=[O:68])[C:55]1[CH:54]=[CH:13][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 131725027HCID 131725027, compound2×

Product 1

HCID 68466455HCID 68466455, compoundYield 100%

Procedure

6N-benzoyl-8-bromo-5′-O-(4,4′-dimethoxytrityl)-2′-deoxyadenosine (Compound 2) (14 gm, 19 mmol) and imidazole (1.94 gm, 28.5 mmol) were dissolved in 100 mL of dry DMF and t-butyldimethyl-silyl chloride (4.3 gm, 28.5 mmol) added to the stirring solution at room temperature. After 4 hrs, TLC on silica gel (2.5% MeOH in CH2Cl2) showed that all starting material had been converted to a new product with higher Rf. The solution was concentrated into a small volume, then about 400 mL of ether was added and washed three times with saturated aqueous NaCl solution. The organic layer was dried over anhydrous Na2SO4, and the filtrate was evaporated to give an off-white foamy product (16.18 gm, 100%). HNMR and ES-MS confirmed the structure.

Workup

  1. concentrationThe solution was concentrated into a small volume
  2. additionabout 400 mL of ether was added
  3. washwashed three times with saturated aqueous NaCl solution
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-eeaf07a5660342c4b35692e169ceedb1
Source dataset
uspto-grants-2005_07
Patent number
US06916612B2

Reaction notes

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