Ethyl Acetate → HCID 178450401, compound

HRID 2099880Notes

Reaction equation

HRID 2099880 reaction equation
C([O-])([O-])=O.[K+].[K+].[C:7]([O:10][C@@H:11]1[C@H:15]([O:16][CH2:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[C@@:14](COS(C)(=O)=O)([CH2:28][O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[O:13][C@@:12]1([SiH:48]([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[N:40]1[CH:47]=[CH:46][C:44](=[O:45])[NH:43][C:41]1=[O:42])(=O)C.CCOC(C)=O>CO>[C:18]1([CH2:17][O:16][C@@H:15]2[C@@:14]3([CH2:7][O:10][C@H:11]2[C@:12]([SiH:48]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)([N:40]2[CH:47]=[CH:46][C:44](=[O:45])[NH:43][C:41]2=[O:42])[O:13]3)[CH2:28][O:29][C:30]([CH3:32])([CH3:31])[CH3:33])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 178476614HCID 178476614, compound

Product 1

HCID 178450401HCID 178450401, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Solid K2CO3 (11.1 g, 80 mmol) was added to a solution of compound 10 (29.4 g, 38 mmol) in methanol (350 mL). After stirring at room temperature for 5 hours, mixture was poured into EtOAc, washed with aqueous NaHCO3, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to a yellow foam. Purification by silica gel chromatography (1% methanol in CH2Cl2) yielded 20.0 g (83%) of nucleoside 11 as a pale yellow foam.

Workup

  1. washwashed with aqueous NaHCO3
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to a yellow foam
  5. customPurification by silica gel chromatography (1% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-92ca82b65c5c435ea836ab0046eb0d98
Source dataset
uspto-grants-2009_08
Patent number
US07569686B1

Reaction notes

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