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

HRID 357489

Reaction equation

HRID 357489 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-81e27642f03d494a8ee70acca574f75e
Source dataset
uspto-grants-1998_11
Patent number
US05840890

Linked notes

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