Methanol → HCID 131731113, compound

HRID 239002Notes

Reaction equation

HRID 239002 reaction equation
[F:1][C@:2]1([CH3:18])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]1=[O:12].[CH3:19][C:20]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])[CH3:21].CO.C1(C)C=CC=CC=1>N1C=CC=CC=1>[Si:23]([O:9][CH2:8][C@H:5]1[O:4][C@@H:3]([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[C@@:2]([F:1])([CH3:18])[C@@H:6]1[OH:7])([C:20]([CH3:22])([CH3:21])[CH3:19])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 28928tert-Butyldimethylsilyl chlorideHCID 113115032'-Deoxy-2'-fluoro-2'-methyluridine

Product 1

HCID 131731113HCID 131731113, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a stirred solution of 2′-deoxy-2′-fluoro-2′-C-methyluridine (3, 81.1 g, 312 mmol) in dry pyridine (750 mL) was added drop-wise a solution of TBDMSCl (103.19 g, 685.6 mmol) in dry pyridine (500 mL) over a period of 45 min at ambient temperature. The reaction was allowed to stir at ambient temperature for 24 h. Methanol (85 mL) was added to the reaction mixture and it was allowed to stir for 10 min and then the solvents were distilled off under reduced pressure. Hot water (45° C.) (1 L) was added to the reaction mass and the mixture extracted with ethyl acetate (2×500 mL), washed with water (1×500 mL). The organic layer was dried over anhydrous sodium sulfate. Ethyl acetate was distilled off and the residue obtained was co-evaporated with toluene (2×500 mL) to give crude 9 as a white foam. Yield=116.9 g (quantitative). 1H NMR (CDCl3, 300 MHz): δ 0.1 (s, 6H), 0.91 (s, 9H), 1.22 (d, 3H, J=21 Hz), 2.50 (s, 2H), 3.75-4.05 (m, 4H), 5.54 (d, 1H, J=9 Hz), 5.73 (s, 1H), 6.0 (d, 1H, J=18 Hz), 7.81 (d, 1H, J=9 Hz), 8.57 (br, s, 1H), 11.1 (s, 1H).

Workup

  1. stirringto stir for 10 min
  2. distillationthe solvents were distilled off under reduced pressure
  3. additionHot water (45° C.) (1 L) was added to the reaction mass
  4. extractionthe mixture extracted with ethyl acetate (2×500 mL)
  5. washwashed with water (1×500 mL)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. distillationEthyl acetate was distilled off
  8. customthe residue obtained

Sources & evidence

ORD record
ord-587766cf05464441883bc2d16374a7ab
Source dataset
uspto-grants-2014_02
Patent number
US08642756B2

Reaction notes

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