HCID 131730078, compound → HCID 25234931, compound

HRID 1881704Notes

Reaction equation

HRID 1881704 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 131730078HCID 131730078, compound

Product 1

HCID 25234931HCID 25234931, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the crude (S)-benzoyloxymethyl-4-(R,S)—(N-benzoylcytosin-1-yl)-1,3-oxathiolane (13.95 g) in a 250 mL round bottom flask, was added approximately 14.0 times (by volume) methanol (194.6 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 (50 mL) and dried under vacuum. The resulting white crystalline solid on analyzing with NMR showed that it is >99% the cis isomer. Isolated yield, 4.8 g (34% yield for the recrystallization, based on the crude). Optical purity: RR/SS: 2.2/97.8.

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 (50 mL)
  9. customdried under vacuum
  10. customIsolated
  11. customyield
  12. custom4.8 g (34% yield for the recrystallization

Sources & evidence

ORD record
ord-510e7137797042d383dccdc2464dc31c
Source dataset
uspto-grants-2012_11
Patent number
US08318934B2

Reaction notes

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