HCID 69267943, compound → HCID 69269388, compound

HRID 395892Notes

Reaction equation

HRID 395892 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH:10]2[O:16][CH:6]1[CH2:7][C:8]([C:18]1[N:26](C3CCCCO3)[C:25]3[C:24](=[O:33])[N:23]([CH2:34][CH2:35][CH3:36])[C:22](=[O:37])[N:21]([CH2:38][CH2:39][CH3:40])[C:20]=3[N:19]=1)([OH:17])[CH2:9]2)=[O:4]>Cl.C1COCC1.CO>[CH3:1][O:2][C:3]([CH:5]1[CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH:10]2[O:16][CH:6]1[CH2:7][C:8]([C:18]1[NH:26][C:25]3[C:24](=[O:33])[N:23]([CH2:34][CH2:35][CH3:36])[C:22](=[O:37])[N:21]([CH2:38][CH2:39][CH3:40])[C:20]=3[N:19]=1)([OH:17])[CH2:9]2)=[O:4]

Participants

4

Reactant 1

HCID 69267943HCID 69267943, compound

Product 1

HCID 69269388HCID 69269388, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 3-[2,6-dioxo-1,3-dipropyl-7-(tetrahydropyran-2-yl)-2,3,6,7-tetrahydro-1H-purin-8-yl]-3-hydroxy-8-oxa-bicyclo[3.2.1]octane-6,7-dicarboxylic acid dimethyl ester (0.060 mmol, 0.030 g) in 1:1 THF/MeOH (6 ml) was added 1N HCl (3 drops). The reaction was stirred at room temperature 3d and then concentrated to dryness. The residue was purified by PLC on a 1 mm layer, eluting with 20% THF/CH2Cl2, providing the title compound (0.0162 g, 56%). 13C NMR (100 MHz, CDCl3): 11.53 (q), 11.50 (q), 21.72 (t), 21.75 (t), 41.74 (t), 43.82 (t), 45.85 (t), 51.02 (d), 52.64 (q), 70.37 (s), 77.12 (d), 107.53 (s), 149.12 (s), 151.17 (s), 156.32 (s), 159.98 (s), 173.36 (s).

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was purified by PLC on a 1 mm layer
  3. washeluting with 20% THF/CH2Cl2

Sources & evidence

ORD record
ord-37a1e57a3c374db7a205fdc3e64b600d
Source dataset
uspto-grants-2003_08
Patent number
US06605600B1

Reaction notes

Loading…