5'-O-(4,4'-Dimethoxytrityl)-2'-O-[2-(N-methylcarbamoyl)ethyl]uridine → HCID 178485725, compound

HRID 1665823Notes

Reaction equation

HRID 1665823 reaction equation
[CH3:1][O:2][C:3]1[CH:46]=[CH:45][C:6]([C:7]([O:22][CH2:23][C@H:24]2[O:28][C@@H:27]([N:29]3[CH:36]=[CH:35][C:33](=[O:34])[NH:32][C:30]3=[O:31])[C@H:26]([O:37][CH2:38][CH2:39][C:40](=[O:43])[NH:41][CH3:42])[C@@H:25]2[OH:44])([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:51]([N:58]([CH:62]([CH3:64])[CH3:63])[CH:59]([CH3:61])[CH3:60])[O:52]OCCC#N)(C)C.[NH:68]1[C-:72]=NN=N1.[CH:73]([NH2+]C(C)C)(C)[CH3:74]>C(#N)C>[C:72]([CH2:73][CH2:74][PH:51]([O:44][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:45]=[CH:46][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[O:28][C@@H:27]([N:29]2[CH:36]=[CH:35][C:33](=[O:34])[NH:32][C:30]2=[O:31])[C@@H:26]1[O:37][CH2:38][CH2:39][C:40](=[O:43])[NH:41][CH3:42])([N:58]([CH:59]([CH3:60])[CH3:61])[CH:62]([CH3:63])[CH3:64])[OH:52])#[N:68]

Participants

5

Reactant 3

HCID 532538595'-O-(4,4'-Dimethoxytrityl)-2'-O-[2-(N-methylcarbamoyl)ethyl]uridineHCID 866383062-cyanoethoxy N,N,N',N'-tetraisopropylphosphorodiamiditeHCID 178458033HCID 178458033, compound

Product 1

HCID 178485725HCID 178485725, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

The compound (490 mg, 0.77 mmol) prepared in Example 8 was dissolved in dried acetonitrile (2 mL), and 2-cyanoethoxy N,N,N′,N′-tetraisopropylphosphorodiamidite (358 mg, 1.19 mmol) dissolved in dried acetonitrile (2 mL) was added thereto. To the mixture was further added diisopropylammonium 1H-tetrazolide (101 mg, 0.59 mmol), followed by stirring at room temperature for 8 hours. The reaction was terminated by adding water thereto, and dilution with ethyl acetate was carried out. The organic layer was washed with saturated brine three times and a saturated sodium hydrogen carbonate aqueous solution three times. The organic layer was dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography eluting with chloroform:methanol (99:1, v/v) containing 0.5% triethylamine to give the title compound (384 mg, 66%).

Workup

  1. additionwas added
  2. customThe reaction was terminated
  3. additionby adding water
  4. washThe organic layer was washed with saturated brine three times
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. washeluting with chloroform:methanol (99:1
  9. additionv/v) containing 0.5% triethylamine

Sources & evidence

ORD record
ord-4a1b9da55fb0403e8c1380fecb14414f
Source dataset
uspto-grants-2011_10
Patent number
US08039611B2

Reaction notes

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