N,N-Diphenylcarbamic chloride → HCID 131728575, compound

HRID 2262400Notes

Reaction equation

HRID 2262400 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:37]3[N:36]=[C:30]([NH:31][C:32](=[S:35])[NH:33][CH3:34])[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:47]1([N:53]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C:54](Cl)=[O:55])[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.O.C(=O)(O)[O-].[Na+]>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:37]3[N:36]=[C:30]([NH:31][C:32](=[S:35])[NH:33][CH3:34])[N:29]=[C:27]([O:28][C:54](=[O:55])[N:53]([C:57]4[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=4)[C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[C:26]=3[N:25]=[CH:24]2)[CH2:10]1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 65741N,N-Diphenylcarbamic chlorideHCID 81531DiisopropylethylamineHCID 86585896Sodium bicarbonate waterHCID 136773142HCID 136773142, compound

Product 1

HCID 131728575HCID 131728575, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

The above-obtained 3′,5′-bis-O-(tert-butyldimethylsilyl)-2-N-methylthiocarbamoyldeoxyguanosine (1.0 g, 1.76 mmol) was azeotroped with anhydrous pyridine three times and dissolved in anhydrous pyridine (17 mL). To the resulting solution, diisopropylethylamine (511 μL, 3.16 mmol) and then diphenylcarbamoyl chloride (489 mg, 2.11 mmol) were added. The mixture was stirred at room temperature for 0.5 hours, and then sodium bicarbonate water (5 mL) was added thereto to terminate the reaction. Then, the reaction solution was extracted with ethyl acetate (150 mL)/sodium bicarbonate water (120 mL) once and then with ethyl acetate (150 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 (N60: spherical neutral silica gel) with ethyl acetate/40% to 50% hexane to give 3′,5′-bis-O-(tert-butyldimethylsilyl)-6-O-diphenylcarbamoyl-2-N-methylthiocarbamoyldeoxyguanosine (1.09 g, 81%).

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionThen, the reaction solution was extracted with ethyl acetate (150 mL)/sodium bicarbonate water (120 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 (N60: spherical neutral silica gel) with ethyl acetate/40% to 50% hexane

Sources & evidence

ORD record
ord-0d8df933893e4989baf8cc6e90e5fc1e
Source dataset
uspto-grants-2010_12
Patent number
US07851157B1

Reaction notes

Loading…