Potassium Carbonate → [(1S)-1-[(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-[1,3]thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxyoxolan-2-yl]propyl] 2-methylpropanoate

HRID 60774Notes

Reaction equation

HRID 60774 reaction equation
[CH3:1][CH:2]([CH3:30])[C:3]([O:5][C@H:6]([C@@H:9]1[CH2:13][C@@H:12]([O:14]C(=O)C)[C@H:11]([N:18]2[C:22]3[N:23]=[C:24]([NH2:28])[NH:25][C:26](=[O:27])[C:21]=3[S:20][C:19]2=[O:29])[O:10]1)[CH2:7][CH3:8])=[O:4].C([O-])([O-])=O.[K+].[K+]>CO.O1CCCC1>[CH3:30][CH:2]([CH3:1])[C:3]([O:5][C@H:6]([C@@H:9]1[CH2:13][C@@H:12]([OH:14])[C@H:11]([N:18]2[C:22]3[N:23]=[C:24]([NH2:28])[NH:25][C:26](=[O:27])[C:21]=3[S:20][C:19]2=[O:29])[O:10]1)[CH2:7][CH3:8])=[O:4]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 137108748HCID 137108748, compound2×

Product 1

HCID 137108695[(1S)-1-[(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-[1,3]thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxyoxolan-2-yl]propyl] 2-methylpropanoateYield 28.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [(1S)-1-[(2S,4R,5R)-4-acetoxy-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-2-yl]propyl] 2-methylpropanoate (compound 42c, 70 mg, 0.16 mmol) and K2CO3 (13.2 mg, 0.096 mmol) in methanol (0.5 mL) and tetrahydrofuran (2 mL) was stirred at room temperature overnight. The reaction was quenched by addition of acetic acid (1 drop). The resulting mixture was concentrated in vacuo to remove the solvents and the residue was purified by preparative HPLC to afford 18.2 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] 2-methylpropanoate (Example 42) as a pale solid.

Workup

  1. customThe reaction was quenched by addition of acetic acid (1 drop)
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. customto remove the solvents
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-34cf1933b4fe491e97d4fef7abb76a4f
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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