Acetic Acid → 1-[(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]propyl benzoate

HRID 60732Notes

Reaction equation

HRID 60732 reaction equation
[C:1]([O:9][CH:10]([C@@H:13]1[CH2:17][C@@H:16]([O:18]C(=O)C)[C@H:15]([N:22]2[C:26]3[N:27]=[C:28]([NH2:32])[NH:29][C:30](=[O:31])[C:25]=3[S:24][C:23]2=[O:33])[O:14]1)[CH2:11][CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].CC(O)=O>CO>[C:1]([O:9][CH:10]([C@@H:13]1[CH2:17][C@@H:16]([OH:18])[C@H:15]([N:22]2[C:26]3[N:27]=[C:28]([NH2:32])[NH:29][C:30](=[O:31])[C:25]=3[S:24][C:23]2=[O:33])[O:14]1)[CH2:11][CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 1371087541-[(2S,4R,5R)-4-acetoxy-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-2-yl]propyl benzoate2×

Product 1

HCID 1371087091-[(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]propyl benzoateYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[(2S,4R,5R)-4-acetoxy-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-2-yl]propyl benzoate (compound 26c, 4.98 g, 10.5 mmol) in methanol (105 mL) was added K2CO3 (1.38 g, 10.0 mmol). After being stirred at room temperature for 1 hour, the reaction was adjusted to pH 7.0 with HOAc (1.2 g, 20.0 mmol), concentrated in vacuo and the residue was purified by column chromatography on silica gel (eluting with 1:200 methanol in DCM) to afford 4.5 g of 1-[(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]propyl benzoate (compound 26d) as a light brown solid. MS obsd. (ESI+) [(M+H)+]: 433.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was purified by column chromatography on silica gel (eluting with 1:200 methanol in DCM)

Sources & evidence

ORD record
ord-8204f4601a2b4a83945ce7071fab4b3e
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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