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

HRID 1871582

반응식

HRID 1871582 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 66995Ethyl orthopropionate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-90a6d401741d41d783aaf2b9151ba6ee
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06103901

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