5'-O-(4,4'-Dimethoxytrityl)-2'-O-[2-(N-methylcarbamoyl)ethyl]-4-N-acetylcytidine → HCID 178485724, compound

HRID 1665826

Reaction equation

HRID 1665826 reaction equation
[CH3:1][O:2][C:3]1[CH:49]=[CH:48][C:6]([C:7]([O:22][CH2:23][C@H:24]2[O:28][C@@H:27]([N:29]3[CH:39]=[CH:38][C:33]([NH:34][C:35](=[O:37])[CH3:36])=[N:32][C:30]3=[O:31])[C@H:26]([O:40][CH2:41][CH2:42][C:43](=[O:46])[NH:44][CH3:45])[C@@H:25]2[OH:47])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.C(N(C(C)C)[P:54]([N:61]([CH:65]([CH3:67])[CH3:66])[CH:62]([CH3:64])[CH3:63])[O:55]OCCC#N)(C)C.[NH:71]1[C-:75]=NN=N1.[CH:76]([NH2+]C(C)C)(C)[CH3:77]>C(#N)C>[C:75]([CH2:76][CH2:77][PH:54]([O:47][C@@H:25]1[C@@H:24]([CH2:23][O:22][C:7]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[C:6]2[CH:48]=[CH:49][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[O:28][C@@H:27]([N:29]2[CH:39]=[CH:38][C:33]([NH:34][C:35](=[O:37])[CH3:36])=[N:32][C:30]2=[O:31])[C@@H:26]1[O:40][CH2:41][CH2:42][C:43](=[O:46])[NH:44][CH3:45])([N:61]([CH:62]([CH3:63])[CH3:64])[CH:65]([CH3:66])[CH3:67])[OH:55])#[N:71]

Participants

5

Reactant 3

HCID 532532925'-O-(4,4'-Dimethoxytrityl)-2'-O-[2-(N-methylcarbamoyl)ethyl]-4-N-acetylcytidineHCID 866383062-cyanoethoxy N,N,N',N'-tetraisopropylphosphorodiamiditeHCID 178458033HCID 178458033, compound

Product 1

HCID 178485724HCID 178485724, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

The compound (480 mg, 0.71 mmol) prepared in Example 24 was dissolved in dried acetonitrile (2 mL). To the solution was added 2-cyanoethoxy N,N,N′,N′-tetraisopropylphosphorodiamidite (343 μL, 1.07 mmol) dissolved in dried acetonitrile (2 mL) and then diisopropylammonium 1H-tetrazolide (92 mg, 0.54 mmol), followed by vigorous stirring at room temperature for 15 hours. The reaction was terminated with a small amount of water, and then the reaction system was concentrated under reduced pressure, diluted with chloroform, and washed with saturated brine. The organic layer was dried with anhydrous sodium sulfate, and filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography eluting with chloroform:methanol:triethylamine (98:1.5:0.5) to give the title compound (300 mg, 0.34 mmol).

Workup

  1. customThe reaction was terminated with a small amount of water
  2. concentrationthe reaction system was concentrated under reduced pressure
  3. additiondiluted with chloroform
  4. washwashed with saturated brine
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate, and filtrate
  6. concentrationwas concentrated under reduced pressure
  7. washeluting with chloroform:methanol:triethylamine (98:1.5:0.5)

Sources & evidence

ORD record
ord-daea591bed8c44648f844e41ec12ab51
Source dataset
uspto-grants-2011_10
Patent number
US08039611B2

Linked notes

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