Acetic Acid → HCID 137108729, compound

HRID 60702Notes

Reaction equation

HRID 60702 reaction equation
[C:1]([O:4][C@H:5]([C@H:8]1[O:12][C@@H:11]([N:13]2[C:17]3[N:18]=[C:19]([NH2:23])[NH:20][C:21](=[O:22])[C:16]=3[S:15][C:14]2=[O:24])[C@@H:10](CC([O-])=O)[CH2:9]1)[CH2:6][CH3:7])(=[O:3])[CH3:2].C([O-])([O-])=[O:30].[K+].[K+].CC(O)=O>CO>[NH2:23][C:19]1[NH:20][C:21](=[O:22])[C:16]2[S:15][C:14](=[O:24])[N:13]([C@@H:11]3[O:12][C@H:8]([C@@H:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:6][CH3:7])[CH2:9][C@H:10]3[OH:30])[C:17]=2[N:18]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 137190216HCID 137190216, compound2×

Product 1

HCID 137108729HCID 137108729, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [(2R,3R,5S)-5-[(1S)-1-acetoxypropyl]-2-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-3-yl]acetate (compound 6h, 210 mg, 0.5 mmol) in methanol (25 mL) was added K2CO3 (136 mg, 1 mmol). After being stirred at room temperature for 10 min, the reaction was adjusted to pH 7.0 by addition of HOAc (120 mg, 2 mmol), concentrated in vacuo and the residue was purified by preparative HPLC to afford 66.7 mg of [(1S)-1-[(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]propyl]acetate (Example 6) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-21b3ee7749cc4678b343db0cabe2fa93
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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