HCID 25234930, compound → Apricitabine

HRID 1881705Notes

Reaction equation

HRID 1881705 reaction equation
C([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(=O)C3C=CC=CC=3)=[N:19][C:17]2=[O:18])[CH2:13][O:12]1)(=O)C1C=CC=CC=1>N>[OH:9][CH2:10][C@H:11]1[S:15][C@@H:14]([N:16]2[CH:31]=[CH:30][C:20]([NH2:21])=[N:19][C:17]2=[O:18])[CH2:13][O:12]1

Participants

3

Reactant 1

HCID 25234930HCID 25234930, compound

Product 1

HCID 455041Apricitabine

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

2-(R)-benzoyloxymethyl-4-(R)—(N-benzoylcytosin-1-yl)-1,3-oxathiolane (15 g, 0.028 mol) was dissolved in a methanolic ammonia (approximately 2M) solution (250 mL). The initial slurry was stirred overnight. After overnight stirring, the resulting clear solution was filtered through celite, evaporated to dryness and slurried in acetone (100 mL). This yielded off-white powdery solid which was filtered and washed with acetone (2×25 mL), and dried to yield the product. 6.5 g (94%).

Workup

  1. stirringAfter overnight stirring
  2. filtrationthe resulting clear solution was filtered through celite
  3. customevaporated to dryness
  4. filtrationThis yielded off-white powdery solid which was filtered
  5. washwashed with acetone (2×25 mL)
  6. customdried
  7. customto yield the product

Sources & evidence

ORD record
ord-8dc363a5b27a4881b04796ad5fefc4e5
Source dataset
uspto-grants-2012_11
Patent number
US08318934B2

Reaction notes

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