HCID 59609006, compound → HCID 25234930, compound

HRID 1881703Notes

Reaction equation

HRID 1881703 reaction equation
[C:1]([O:9][CH2:10][C@H:11]1[S:15][CH:14]([N:16]2[CH:31]=[CH:30][C:20]([NH:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:19][C:17]2=[O:18])[CH2:13][O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[C:1]([O:9][CH2:10][C@H:11]1[S:15][C@@H:14]([N:16]2[CH:31]=[CH:30][C:20]([NH:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:19][C:17]2=[O:18])[CH2:13][O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 59609006HCID 59609006, compound

Product 1

HCID 25234930HCID 25234930, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the crude (R)-benzoyloxymethyl-4-(R,S)-(N-benzoylcytosin-1-yl)-1,3-oxathiolane (8.0 g) in a 100 mL round bottom flask, was added approximately 14.0 times (by volume) methanol (112 mL) and the mixture was refluxed till a clear solution could be seen. This was then allowed to cool without stirring overnight. The resulting crystallized product was then filtered, followed by washing with methanol (50 mL). Once all the mother liquor and the subsequent washing had passed through, the resulting crystallized white product was re-washed slowly with methanol (2×100 mL) and dried under vacuum. The resulting white crystalline solid on analyzing with NMR showed that it is >99% the cis isomer. Isolated yield, 3.36 g (42% yield for the recrystallization, based on the crude). Optical purity: RR/SS: 98.1/1.9.

Workup

  1. temperaturethe mixture was refluxed till a clear solution
  2. temperatureto cool
  3. customThe resulting crystallized product
  4. filtrationwas then filtered
  5. washby washing with methanol (50 mL)
  6. washOnce all the mother liquor and the subsequent washing
  7. customcrystallized white product
  8. washwas re-washed slowly with methanol (2×100 mL)
  9. customdried under vacuum
  10. customIsolated
  11. customyield
  12. custom3.36 g (42% yield for the recrystallization

Sources & evidence

ORD record
ord-effafe7d14d847e2907ba6d3d31dc865
Source dataset
uspto-grants-2012_11
Patent number
US08318934B2

Reaction notes

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