Isopropanol → Amdoxovir

HRID 227462Notes

Reaction equation

HRID 227462 reaction equation
C([O:6][CH2:7][C@H:8]1[O:12][C@@H:11]([N:13]2[CH:21]=[N:20][C:19]3[C:14]2=[N:15][C:16]([NH2:23])=[N:17][C:18]=3[NH2:22])[CH2:10][O:9]1)(=O)C(C)C.CC(O)C>N>[NH2:23][C:16]1[N:15]=[C:14]2[C:19]([N:20]=[CH:21][N:13]2[C@H:11]2[CH2:10][O:9][C@@H:8]([CH2:7][OH:6])[O:12]2)=[C:18]([NH2:22])[N:17]=1

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 16050140(2R,4R)-2-isobutyryloxymethyl-4-(2,6-diaminopurin-9-yl)-1,3-dioxolane

Product 1

HCID 124088AmdoxovirYield 83%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Conditions

Temperature
25 °C

Procedure

31.05 g of (2R,4R)-2-isobutyryloxymethyl-4-(2,6-diaminopurin-9-yl)-1,3-dioxolane×2-propanol (cf. Example 4) were dissolved in 310 ml of NH3-saturated methanol. The solution was stirred at 25° C. for 15 h, and the solvent was distilled off in vacuo. The residue was recrystallized from ethanol/water. 17.10 g (83%) of (−)-DAPD were obtained as colorless crystals.

Workup

  1. distillationthe solvent was distilled off in vacuo
  2. customThe residue was recrystallized from ethanol/water

Sources & evidence

ORD record
ord-b8b1fe9c93ec488987e4594a347b4e5b
Source dataset
uspto-grants-2009_07
Patent number
US07560550B2

Reaction notes

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