Imidazole → (1R,2S,3R,5R)-3-[6-Amino-9H-purin-9-yl]-5-[((2,3-dimethylbut-2-yl)dimethylsilyloxy)methyl]-1,2-cyclopentanediol

HRID 466240

반응식

HRID 466240 반응식
[CH:1]1[N:6]=[C:5]2[N:7]([C@H:10]3[C@H:14]([OH:15])[C@H:13]([OH:16])[C@@H:12]([CH2:17][OH:18])[CH2:11]3)[CH:8]=[N:9][C:4]2=[C:3]([NH2:19])[N:2]=1.CN(C)C=O.N1C=CN=C1.[CH3:30][Si:31](Cl)([CH3:38])[C:32]([CH:35]([CH3:37])[CH3:36])([CH3:34])[CH3:33]>O>[NH2:19][C:3]1[N:2]=[CH:1][N:6]=[C:5]2[C:4]=1[N:9]=[CH:8][N:7]2[C@@H:10]1[CH2:11][C@H:12]([CH2:17][O:18][Si:31]([C:32]([CH3:34])([CH:35]([CH3:37])[CH3:36])[CH3:33])([CH3:38])[CH3:30])[C@@H:13]([OH:16])[C@H:14]1[OH:15]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 65269AristeromycinHCID 144239Dimethylthexylsilyl chloride2회

생성물 1

HCID 15089637(1R,2S,3R,5R)-3-[6-Amino-9H-purin-9-yl]-5-[((2,3-dimethylbut-2-yl)dimethylsilyloxy)methyl]-1,2-cyclopentanediol

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of aristeromycin (50 g) and dimethylformamide (250 ml) was stirred at room temperature and imidazole (50 g) and then dimethylthexylsilyl chloride (10 ml) were added. Three further 10 ml portions of dimethylthexylsilyl chloride were added after 20 min, 1 h and 1.75 h. After 4 h the resulting mixture was poured into rapidly stirred water (2.5 L). The suspension was filtered and the residue washed with water (2×250 ml). The air dried solid was added to di-isopropyl ether (500 ml) and stirred for 20 min. The suspension was filtered and the residue collected, stirred with diethyl ether (500 ml) and filtered to give the title compound (49 g); 1H nmr (DMSO-d6) δ8.13 (1H), 8.09 (1H), 7.18 (2H), 5.03-4.93 (1H), 4.76-4.60 (2H), 4.41-4.28 (1H), 3.88-3.78 (1H), 3.72-3.57 (2H), 2.28-1.70 (3H), 1.67-1.52 (1H), 0.95-0.75 (12H), 0.1 (6H).

후처리

  1. filtrationThe suspension was filtered
  2. washthe residue washed with water (2×250 ml)
  3. customThe air dried solid
  4. additionwas added to di-isopropyl ether (500 ml)
  5. stirringstirred for 20 min
  6. filtrationThe suspension was filtered
  7. customthe residue collected
  8. stirringstirred with diethyl ether (500 ml)
  9. filtrationfiltered

출처 및 근거

ORD 기록
ord-c0be78fd77224f0b9ea87f495985fd6e
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155112

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