HCID 25234931, compound → (+)-DOTC

HRID 1881706Notes

Reaction equation

HRID 1881706 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 25234931HCID 25234931, compound

Product 1

HCID 468214(+)-DOTC

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

2-(S)-benzoyloxymethyl-4-(S)—(N-benzoylcytosin-1-yl)-1,3-oxathiolane (1.0 g, 0.0022 mol) was dissolved in a methanolic ammonia (approximately 2M) solution (20 mL). The initial slurry was stirred overnight. After overnight stirring, the resulting clear solution was evaporated to dryness and slurried in acetone (20 mL). This yielded off-white powdery solid which was filtered and washed with acetone (2×10 mL), and dried to yield the product. 0.47 g (88%).

Workup

  1. stirringAfter overnight stirring
  2. customthe resulting clear solution was evaporated to dryness
  3. filtrationThis yielded off-white powdery solid which was filtered
  4. washwashed with acetone (2×10 mL)
  5. customdried
  6. customto yield the product

Sources & evidence

ORD record
ord-6b36288fdd60451b99de7292bb93f010
Source dataset
uspto-grants-2012_11
Patent number
US08318934B2

Reaction notes

Loading…