Iodine → HCID 18767661, compound

HRID 480119Notes

Reaction equation

HRID 480119 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-3632855a1569468697bc6e560742270d
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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