Iodine → HCID 18767661, compound

HRID 2105651Notes

Reaction equation

HRID 2105651 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:18]3[N:17]=[C:16]([C:19]45[CH2:26][CH2:25][C:22]([C:27]([OH:29])=[O:28])([CH2:23][CH2:24]4)[CH2:21][CH2:20]5)[NH:15][C:14]=3[C:13](=[O:30])[N:12]([CH2:31][CH2:32][CH3:33])[C:11]2=[O:34])=[CH:4][CH:3]=1.[OH-].[Na+].[I:37]I>O.C(O)C>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:18]3[N:17]=[C:16]([C:19]45[CH2:20][CH2:21][C:22]([C:27]([OH:29])=[O:28])([CH2:25][CH2:26]4)[CH2:23][CH2:24]5)[NH:15][C:14]=3[C:13](=[O:30])[N:12]([CH2:31][CH2:32][CH3:33])[C:11]2=[O:34])=[CH:4][C:3]=1[I:37]

Participants

6

Reactant 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 18767719HCID 18767719, compound

Product 1

HCID 18767661HCID 18767661, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 50 mg 4-{3-[2-(4-Hydroxy-phenyl)-ethyl]-2,6-dioxo-1-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl}-bicyclo[2.2.2]octane-1-carboxylic acid (Example 27a) (0.107 mmol) in water (10 ml) containing 1 eq. of 1N NaOH (110 μL) was added at rt a solution of 30 mg of iodine (0.107 mmol) in ethanol (1 ml). The reaction mixture was concentrated in vacuo and the crude product purified by preparative chromatography to afford 12 mg (20%) of desired product (MH+=592.89).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude product purified by preparative chromatography

Sources & evidence

ORD record
ord-bac5ec59399a4a399973d26ccb8366e9
Source dataset
uspto-grants-2009_08
Patent number
US07579354B2

Reaction notes

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