Ethyl Acetate → HCID 137190222, compound

HRID 60762Notes

Reaction equation

HRID 60762 reaction equation
FC(F)(F)S([O:6][C:7]1[C:8]2[S:16][C:15](=[O:17])[N:14]([C@H:18]3[C@H:22](OS(C(F)(F)F)(=O)=O)[CH2:21][C@@H:20]([CH2:31][O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[O:19]3)[C:9]=2[N:10]=[C:11]([NH2:13])[N:12]=1)(=O)=O.[C-:42]#[N:43].[Na+].CCOC(C)=O>CN(C=O)C>[NH2:13][C:11]1[NH:12][C:7](=[O:6])[C:8]2[S:16][C:15](=[O:17])[N:14]([C@H:18]3[C@H:22]([C:42]#[N:43])[CH2:21][C@@H:20]([CH2:31][O:32][Si:33]([C:36]([CH3:38])([CH3:39])[CH3:37])([CH3:34])[CH3:35])[O:19]3)[C:9]=2[N:10]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 131737111HCID 131737111, compound2×

Product 1

HCID 137190222HCID 137190222, compoundYield 118%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of [5-amino-3-[(2R,3R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(trifluoromethylsulfonyloxy)tetrahydrofuran-2-yl]-2-oxo-thiazolo[4,5-d]pyrimidin-7-yl] trifluoromethanesulfonate (compound 38g, crude, 120 mg, 0.2 mmol) in DMF (2 mL) was added sodium cyanide (100 mg, 2.3 mmol). After being stirred at room temperature for 2 hours, the resulting solution was diluted by EtOAc, washed with brine, dried over Na2SO4 and concentrated in vacuo to afford 100 mg crude product of (2R,3S,5S)-2-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]tetrahydrofuran-3-carbonitrile (compound 38h), which was used in next step without further purification. MS obsd. (ESI+) [(M+H)+]: 424.

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-da2a072094eb4c5aa4d08eb809edbc90
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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