Acetic Acid → 2-((2-Amino-6-oxo-1,6-dihydro-9H-purin-9-YL)methoxy)-3-hydroxypropyl propionate, (+-)-

HRID 1871582Notes

Reaction equation

HRID 1871582 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:18])[C:5]2[N:6]=[CH:7][N:8]([CH2:11][O:12][CH:13]([CH2:16][OH:17])[CH2:14][OH:15])[C:9]=2[N:10]=1.CS(C)=O.[C:23]1([CH3:33])C=CC(S([O-])(=O)=O)=C[CH:24]=1.[NH+]1C=CC=CC=1.C(O)(=[O:42])C>C(OCC)(OCC)(OCC)CC.C(O)C>[NH2:1][C:2]1[NH:3][C:4](=[O:18])[C:5]2[N:6]=[CH:7][N:8]([CH2:11][O:12][CH:13]([CH2:16][O:17][C:24](=[O:42])[CH2:23][CH3:33])[CH2:14][OH:15])[C:9]=2[N:10]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 135398740Ganciclovir

Product 1

HCID 1355154092-((2-Amino-6-oxo-1,6-dihydro-9H-purin-9-YL)methoxy)-3-hydroxypropyl propionate, (+-)-

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 66995Ethyl orthopropionateSolvent

Procedure

To 5 g of 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-1,3-propanediol (ganciclovir) in 20 ml of triethyl orthopropionate was added 5 ml of dimethylsulfoxide (DMSO) and 0.25 g of pyridinium p-toluenesulfonate (PPTS). The slurry was stirred at room temperature for 4.5 hours. 70% Aqueous acetic acid (10 ml) was added and the mixture was stirred for 2 hours. Then 30 ml of ethanol was added, the mixture was stirred for another 0.5 hour and filtered. The white solid was washed twice with 50 ml each of ethanol and air dried to give 4.77 g of product. 1H-NMR: δ 0.9 (t,3H), 2.05 (q,2H), 3.32 (m,2H), 3.8 (m,1H), 3.85 (dd,1H), 4.0 (dd,1H), 4.8 (t,1H), 5.35 (ad,2H), 6.45 (br s, 2H), 7.75 (s,1H), 10.6 (s,1H).

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. stirringthe mixture was stirred for another 0.5 hour
  3. filtrationfiltered
  4. washThe white solid was washed twice with 50 ml each of ethanol and air
  5. customdried

Sources & evidence

ORD record
ord-90a6d401741d41d783aaf2b9151ba6ee
Source dataset
uspto-grants-2000_08
Patent number
US06103901

Reaction notes

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