Methanol → Famciclovir

HRID 1268155노트

반응식

HRID 1268155 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

HCID 3324Famciclovir수율 70%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 3776Isopropanol용매HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-dfd0fd26c1a749f19a918feecabcbf28
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06555685B1

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