HCID 67078874, compound → HCID 18767658, compound

HRID 2105662Notes

Reaction equation

HRID 2105662 reaction equation
C[O:2][C:3]([CH:5]1[CH2:12][CH2:11][C:10]2([C:14]3[NH:22][C:21]4[C:20](=[O:23])[N:19]([CH2:24][CH2:25][CH3:26])[C:18](=[O:27])[N:17]([CH2:28][CH2:29][CH3:30])[C:16]=4[N:15]=3)[O:13][CH:6]1[CH2:7][CH2:8][CH2:9]2)=[O:4]>CO>[O:27]=[C:18]1[N:17]([CH2:28][CH2:29][CH3:30])[C:16]2[N:15]=[C:14]([C:10]34[O:13][CH:6]([CH2:7][CH2:8][CH2:9]3)[CH:5]([C:3]([OH:4])=[O:2])[CH2:12][CH2:11]4)[NH:22][C:21]=2[C:20](=[O:23])[N:19]1[CH2:24][CH2:25][CH3:26]

Participants

3

Reactant 1

HCID 67078874HCID 67078874, compound

Product 1

HCID 18767658HCID 18767658, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-9-oxa-bicyclo[3.3.1]nonane-2-carboxylic acid methyl ester (50 mg, from step 2) was taken in MeOH (5 ml) LiOH (15 mg) was added and stirred at rt overnight. Next day MeOH was removed under reduced pressure, diluted with water and extracted with ethyl acetate. Aqueous layer was acidified with 1N HCl, extracted with ethyl acetate (3×25 ml). Combined organic layer was washed with brine, and dried over Na2SO4. Concentration of the solvent gave a white solid, which was purified by crystallizing from ether. Mass (ES+ 405)

Workup

  1. additionwas added
  2. customNext day MeOH was removed under reduced pressure
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. extractionextracted with ethyl acetate (3×25 ml)
  6. washCombined organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. customConcentration of the solvent gave a white solid, which
  9. customwas purified
  10. customby crystallizing from ether

Sources & evidence

ORD record
ord-67ba5254cf7549188f379dda919b3a2e
Source dataset
uspto-grants-2009_08
Patent number
US07579354B2

Reaction notes

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