Potassium Carbonate → N-{(1S,2R,3S,4R)-4-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-hydroxy-acetamide

HRID 1929772Notes

Reaction equation

HRID 1929772 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([NH:16][C:17]([CH2:19][O:20]C(=O)C)=[O:18])[C@@H:13]([OH:24])[C@H:12]2[OH:25])=[C:4]([NH:26][CH2:27][CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([NH:16][C:17](=[O:18])[CH2:19][OH:20])[C@@H:13]([OH:24])[C@H:12]2[OH:25])=[C:4]([NH:26][CH2:27][CH:28]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86637573Acetic acid {(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentylcarbamoyl}-methyl ester

Product 1

HCID 86637575N-{(1S,2R,3S,4R)-4-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-hydroxy-acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of acetic acid {(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentylcarbamoyl}-methyl ester (0.2 g, 0.35 mmol) in MeOH (10 mL) is added potassium carbonate (0.098 g, 0.7 mmol) and the reaction mixture is stirred at room temperature for 1 hour. The solvent is removed in vacuo and the solvent is partitioned between DCM and water. The organic portion is separated, dried (MgSO4) and concentrated in vacuo to afford the title product. MS (ES+) m/e 522.4/524.5 (MH+).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe solvent is partitioned between DCM and water
  3. customThe organic portion is separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5ce5f4a9cb104e95a280ad1037fd1953
Source dataset
uspto-grants-2012_05
Patent number
US08188100B2

Reaction notes

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