Phosphoric acid dibenzyl ester 4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl ester → Phosphoric acid mono-[4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl] ester

HRID 480135Notes

Reaction equation

HRID 480135 reaction equation
[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[N:8]=[C:7]([C:14]34[CH2:21][CH2:20][C:17]([O:22][P:23](=[O:40])([O:32]CC5C=CC=CC=5)[O:24]CC5C=CC=CC=5)([CH2:18][CH2:19]3)[CH2:16][CH2:15]4)[NH:6][C:5]=2[C:4](=[O:41])[N:3]1[CH2:42][CH2:43][CH3:44]>CO.C1COCC1.[Pd]>[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[N:8]=[C:7]([C:14]34[CH2:19][CH2:18][C:17]([O:22][P:23](=[O:24])([OH:32])[OH:40])([CH2:16][CH2:15]3)[CH2:20][CH2:21]4)[NH:6][C:5]=2[C:4](=[O:41])[N:3]1[CH2:42][CH2:43][CH3:44]

Participants

5

Reactant 1

HCID 67078989Phosphoric acid dibenzyl ester 4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl ester

Product 1

HCID 9954897Phosphoric acid mono-[4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl] esterYield 86%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Phosphoric acid dibenzyl ester 4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl ester was dissolved in a mixture of 15 ml methanol and 10 ml of THF, Pd/C (10%, 50 mg) was added to the mixture. Hydrogenation was taken place at 50 psi for 8 h. Pd/C was filtered off and solvent was evaporated off. The residue was recrystallized in a mixture of methanol and ethyl acetate to get 190 mg title product (yield 86%). MS (M+1, 441)

Workup

  1. additionwas added to the mixture
  2. customfor 8 h
  3. filtrationPd/C was filtered off
  4. customsolvent was evaporated off
  5. customThe residue was recrystallized in a mixture of methanol and ethyl acetate

Sources & evidence

ORD record
ord-f7b2ee05ec2f42109af09dc2cda35d51
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

Loading…