Trisodium Phosphate → Isotorabine

HRID 549802Notes

Reaction equation

HRID 549802 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:24][C@H:23]([CH2:25][O:26]C(=O)C)[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:13]3[O:14][C:15](=[O:17])[CH3:16])[C:6]=2[N:7]=1.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>CC(C)=O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:24][C@H:23]([CH2:25][OH:26])[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:13]3[O:14][C:15](=[O:17])[CH3:16])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 24243Trisodium PhosphateHCID 116332675-Amino-3-(2',3,5'-tri-O-acetyl-beta-D-ribofuranosyl)-3H-thiazolo[4,5-d]pyrimidin-2-one

Product 1

HCID 11234476Isotorabine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a clear solution of 78 (500 mg) in acetone (5 mL) was added sodium phosphate buffer (pH=7.0, 0.1 M, 25 mL), upon which the solution became cloudy (white precipitate). Candida antarctica lipase resin (250 mg) was added to the mixture and the suspension was subsequently gently shaken for 10 h at room temperature. The resulting clear mixture was filtered, and organic solvent was removed under vacuum. The aqueous solution was then extracted with ethyl acetate (3×25 mL) and the organic layers were combined, dried over MgSO4, and concentrated. The resulting solid could be further purified in a manner similar to that described in Example 43, step 3.

Workup

  1. filtrationThe resulting clear mixture was filtered
  2. customorganic solvent was removed under vacuum
  3. extractionThe aqueous solution was then extracted with ethyl acetate (3×25 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe resulting solid could be further purified in a manner similar to

Sources & evidence

ORD record
ord-e49683438036481dbb53493d80064f2a
Source dataset
uspto-grants-2011_05
Patent number
US07943759B2

Reaction notes

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