Toluene → HCID 86761227, compound

HRID 2262393Notes

Reaction equation

HRID 2262393 reaction equation
[Si]([O:8][C@@H:9]1[C@@H:13]([CH2:14][O:15][Si](C(C)(C)C)(C)C)[O:12][C@@H:11]([N:23]2[C:52]3[N:51]=[C:45]([NH:46][C:47](=[O:50])[NH:48][CH3:49])[N:44]=[C:27]([O:28][C:29](=[O:43])[N:30]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:26]=3[N:25]=[CH:24]2)[CH2:10]1)(C(C)(C)C)(C)C.C(N(CC)CC)C.C1(C)C=CC=CC=1>O1CCCC1>[C:37]1([N:30]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:29]([O:28][C:27]2[C:26]3[N:25]=[CH:24][N:23]([C:52]=3[N:51]=[C:45]([NH:46][C:47](=[O:50])[NH:48][CH3:49])[N:44]=2)[C@@H:11]2[O:12][C@H:13]([CH2:14][OH:15])[C@@H:9]([OH:8])[CH2:10]2)=[O:43])[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 8471TriethylamineHCID 131728573HCID 131728573, compound

Product 1

HCID 86761227HCID 86761227, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The above-obtained 3′,5′-bis-O-(tert-butyldimethylsilyl)-6-O-diphenylcarbamoyl-2-N-methylcarbamoyldeoxyguanosine (1.13 g, 52 mmol) was azeotroped with anhydrous tetrahydrofuran three times and then dissolved in anhydrous tetrahydrofuran (15 mL), and triethylamine 3 hydrogen fluoride (743 μL, 4.56 mmol) was added thereto. The mixture was stirred at room temperature overnight. Then, after addition of toluene (5 mL), the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (C200) with methanol/5% to 6% chloroform, and then ethyl acetate (5 mL) and diethyl ether (15 mL) were added thereto for precipitation. Then, the precipitate was purified by filtration to give 6-O-diphenylcarbamoyl-2-N-methylcarbamoyldeoxyguanosine (643 mg, 81%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (C200) with methanol/5% to 6% chloroform
  3. additionethyl acetate (5 mL) and diethyl ether (15 mL) were added
  4. customfor precipitation
  5. filtrationThen, the precipitate was purified by filtration

Sources & evidence

ORD record
ord-05d68469c83f4a44bc6123b384249bce
Source dataset
uspto-grants-2010_12
Patent number
US07851157B1

Reaction notes

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