Ethanol → 3-[4-(6-Methylsulfanyl-2-oxo-3-propyl-3,7-dihydro-2H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-propionic acid methyl ester

HRID 395285Notes

Reaction equation

HRID 395285 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][C:6]12[CH2:13][CH2:12][C:9]([C:14]3[NH:22][C:21]4[C:20](=[S:23])[NH:19][C:18](=[O:24])[N:17]([CH2:25][CH2:26][CH3:27])[C:16]=4[N:15]=3)([CH2:10][CH2:11]1)[CH2:8][CH2:7]2.[OH-].[Na+].[CH3:31]CO>O>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][C:6]12[CH2:7][CH2:8][C:9]([C:14]3[NH:22][C:21]4[C:20]([S:23][CH3:31])=[N:19][C:18](=[O:24])[N:17]([CH2:25][CH2:26][CH3:27])[C:16]=4[N:15]=3)([CH2:10][CH2:11]1)[CH2:12][CH2:13]2

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 865856363-[4-(2-Oxo-3-propyl-6-thioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-propionic acid methyl ester

Product 1

HCID 119944193-[4-(6-Methylsulfanyl-2-oxo-3-propyl-3,7-dihydro-2H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3-[4-(2-Oxo-3-propyl-6-thioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-propionic acid methyl ester (100 mg) was dissolved in 2 mL of EtOH and 1 mL of H2O. NaOH (20 mg) was added as a solution in 1 mL of H2O, followed by Mel (23 uL, 1.5 eq). The resulting reaction mixture was stirred at rt for 30 min. It was then extracted with EtOAc. The organic layer was dried (Na2SO4) and concentrated under reduced pressure to afford 105 mg of the titled compound.

Workup

  1. customThe resulting reaction mixture
  2. extractionIt was then extracted with EtOAc
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5392a47d2fd74f4a955a30c76a3c4fb5
Source dataset
uspto-grants-2003_08
Patent number
US06605601B2

Reaction notes

Loading…