Trifluoroacetic acid → Valomaciclovir Stearate

HRID 362605Notes

Reaction equation

HRID 362605 reaction equation
C(OC([NH:8][C@H:9]([C:13]([O:15][CH2:16][CH2:17][C@@H:18]([CH2:31][O:32][C:33](=[O:51])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH2:19][N:20]1[CH:28]=[N:27][C:26]2[C:25](=[O:29])[NH:24][C:23]([NH2:30])=[N:22][C:21]1=2)=[O:14])[CH:10]([CH3:12])[CH3:11])=O)(C)(C)C.FC(F)(F)C(O)=O>O>[C:33]([O:32][CH2:31][C@H:18]([CH2:17][CH2:16][O:15][C:13](=[O:14])[C@H:9]([CH:10]([CH3:12])[CH3:11])[NH2:8])[CH2:19][N:20]1[CH:28]=[N:27][C:26]2[C:25](=[O:29])[NH:24][C:23]([NH2:30])=[N:22][C:21]1=2)(=[O:51])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 135796494(R)-9-(2-stearoyloxymethyl-4-(N-tert-butoxycarbonyl-L-valyloxy)butyl)guanine

Product 1

HCID 135399823Valomaciclovir Stearate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The product from step b) (138 mg, 0.192 mmol) was cooled in an ice bath and trifluoroacetic acid (5 ml) was added. The solution was kept in the ice bath for 45 minutes and was then evaporated to give an oil. Water (0.5 to 1 ml) was added and evaporated twice. The residue was once more dissolved in water (5 ml), filtered and freeze-dried to give 148 mg of the desired product as the bistrifluoroacetate salt.

Workup

  1. customwas then evaporated
  2. customto give an oil
  3. customevaporated twice
  4. dissolutionThe residue was once more dissolved in water (5 ml)
  5. filtrationfiltered
  6. customfreeze-dried

Sources & evidence

ORD record
ord-c5af869df5ad4b91b891e100a3d04c53
Source dataset
uspto-grants-1999_02
Patent number
US05869493

Reaction notes

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