N,N-Diphenylcarbamic chloride → HCID 131728574, compound

HRID 2262396Notes

Reaction equation

HRID 2262396 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@H:13]([CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[O:12][C@@H:11]([N:23]2[C:36]3[N:35]=[C:30]([NH:31][C:32](=[O:34])[NH2:33])[NH:29][C:27](=[O:28])[C:26]=3[N:25]=[CH:24]2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[C:46]1([N:52]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:53](Cl)=[O:54])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>N1C=CC=CC=1>[Si:1]([O:8][C@@H:9]1[C@@H:13]([CH2:14][O:15][Si:16]([C:19]([CH3:20])([CH3:21])[CH3:22])([CH3:17])[CH3:18])[O:12][C@@H:11]([N:23]2[C:36]3[N:35]=[C:30]([NH:31][C:32](=[O:34])[NH2:33])[N:29]=[C:27]([O:28][C:53](=[O:54])[N:52]([C:56]4[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=4)[C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[C:26]=3[N:25]=[CH:24]2)[CH2:10]1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 65741N,N-Diphenylcarbamic chlorideHCID 81531DiisopropylethylamineHCID 136773140HCID 136773140, compound

Product 1

HCID 131728574HCID 131728574, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

The above-obtained 3′,5′-bis-O-(tert-butyldimethylsilyl)-2-N-carbamoyldeoxyguanosine (1.23 g, 2.29 mmol) was azeotroped with anhydrous pyridine three times and then dissolved in anhydrous pyridine (23 mL). To the resulting solution, diisopropylethylamine (797 μL, 4.58 mmol) and then diphenylcarbamoyl chloride (689 mg, 2.98 mmol) were added, and the mixture was stirred at room temperature for 0.5 hours. Then, the reaction was terminated by adding sodium bicarbonate water (5 ml) thereto. The reaction solution was extracted with ethyl acetate (180 mL)/sodium bicarbonate water (150 mL) once and then with ethyl acetate (180 mL)/brine (100 mL) twice. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (C200) with ethyl acetate/50% to 60% hexane to give 3′,5′-bis-O-(tert-butyldimethylsilyl)-2-N-carbamoyl-6-O-diphenylcarbamoyldeoxyguanosine (1.53 g, 91%).

Workup

  1. customThen, the reaction was terminated
  2. additionby adding sodium bicarbonate water (5 ml)
  3. extractionThe reaction solution was extracted with ethyl acetate (180 mL)/sodium bicarbonate water (150 mL) once
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (C200) with ethyl acetate/50% to 60% hexane

Sources & evidence

ORD record
ord-384acf0b18f3447f85912d8a34c051e1
Source dataset
uspto-grants-2010_12
Patent number
US07851157B1

Reaction notes

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