Methanol → Famciclovir

HRID 1268155

Reaction equation

HRID 1268155 reaction equation
Cl.[NH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[CH2:12][CH2:13][CH:14]([CH2:17][OH:18])[CH2:15][OH:16])=[CH:5][N:4]=1.C(N([CH2:24][CH3:25])CC)C.[C:26](OC(=O)C)(=[O:28])[CH3:27].C[OH:34]>CN(C)C1C=CN=CC=1.ClCCl.CC(O)C>[C:26]([O:16][CH2:15][CH:14]([CH2:17][O:18][C:24](=[O:34])[CH3:25])[CH2:13][CH2:12][N:9]1[CH:8]=[N:7][C:6]2[C:10]1=[N:11][C:3]([NH2:2])=[N:4][CH:5]=2)(=[O:28])[CH3:27]

Participants

8

Reactant 4

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 44226540Desacetyl famciclovir hydrochloride

Product 1

HCID 3324FamciclovirYield 70%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 2-amino-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine hydrochloride (0.79 g), 4-dimethylaminopyridine (16 mg) and triethylamine (1.4 ml) in dichloromethane (16 ml) at room temperature was added acetic anhydride (0.57 ml). The resulting mixture was stirred at ambient temperature for 2.25 hours. Methanol (4 ml) was added and the solution stirred for 0.5 hours before being evaporated to dryness. Water (20 ml) was added and the aqueous solution extracted with dichloromethane (3×20 ml). The combined extracts were concentrated to give an oil. This oil was dissolved in 2-propanol (5 ml), the solvent evaporated and the residue recrystallised from 2-propanol (5 ml). The product was collected by filtration, washed with 2-propanol (3 ml) and dried to give the title compound (654 mg, 70%).

Workup

  1. stirringthe solution stirred for 0.5 hours
  2. custombefore being evaporated to dryness
  3. additionWater (20 ml) was added
  4. extractionthe aqueous solution extracted with dichloromethane (3×20 ml)
  5. concentrationThe combined extracts were concentrated
  6. customto give an oil
  7. customthe solvent evaporated
  8. customthe residue recrystallised from 2-propanol (5 ml)
  9. filtrationThe product was collected by filtration
  10. washwashed with 2-propanol (3 ml)
  11. customdried

Sources & evidence

ORD record
ord-dfd0fd26c1a749f19a918feecabcbf28
Source dataset
uspto-grants-2003_04
Patent number
US06555685B1

Linked notes

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