Ammonium Sulfate → 4-Amino-2-phenyl-8-[2-deoxy-3,5-di-O-(4-chlorobenzoyl)-beta-D-ribofuranosyl]-pteridine-7-one

HRID 976934

반응식

HRID 976934 반응식
[NH2:1][C:2]1[C:11]2[C:6](=[N:7][C:8](=[O:12])[CH2:9][N:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1.S([O-])([O-])(=O)=O.[NH4+].[NH4+].[Cl:26][C:27]1[CH:52]=[CH:51][C:30]([C:31]([O:33][C@@H:34]2[C@@H:38]([CH2:39][O:40][C:41](=[O:49])[C:42]3[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=3)[O:37][C@H:36](Cl)[CH2:35]2)=[O:32])=[CH:29][CH:28]=1>C[Si](C)(C)N[Si](C)(C)C.C(Cl)Cl.Cl([O-])(=O)(=O)=O.[Ag+]>[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8](=[O:12])[N:7]([C@@H:36]3[O:37][C@H:38]([CH2:39][O:40][C:41](=[O:49])[C:42]4[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=4)[C@@H:34]([O:33][C:31](=[O:32])[C:30]4[CH:51]=[CH:52][C:27]([Cl:26])=[CH:28][CH:29]=4)[CH2:35]3)[C:6]=2[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1

참가 물질

7

반응물 3

HCID 6097028Ammonium SulfateHCID 9845541alpha-D-erythro-Pentofuranosyl chloride, 2-deoxy-, 3,5-bis(4-chlorobenzoate)HCID 544025114-Amino-2-phenyl-pteridine-7-one

생성물 1

HCID 154039094-Amino-2-phenyl-8-[2-deoxy-3,5-di-O-(4-chlorobenzoyl)-beta-D-ribofuranosyl]-pteridine-7-one

시약·촉매·용매 3

HCID 24562Silver perchlorate촉매HCID 6344Dichloromethane용매HCID 13838Hexamethyldisilazane용매2회

실험 절차

A mixture of 1.0 g (4.2 mmol) of 4-amino-2-phenyl-pteridine-7-one (3) and a few crystals of ammonium sulfate was heated in 100 mL of hexamethyldisilazane (HMDS) under reflux for 4 hours. After cooling the excess HMDS was distilled off in vacuum and the residue dissolved in 100 mL of dry toluene. To the mixture was added 2.17 g (4.6 mmol) of 2-deoxy-3,5-di-O-(4-chlorobenzoyl)-α-D-ribofuranosyl chloride (made as in Example 3, step (a) for the toluyl derivative) and 0.476 g (2.3 mmol) of silver perchlorate. The solution was then stirred under anhydrous conditions for 24 hours at room temperature and then diluted with 200 mL of CH2Cl2. The resulting AgCl precipitate was filtered off through silica and then the filtrate was treated with 100 mL of a saturated aqueous solution of sodium bicarbonate followed by 100 mL of a saturated aqueous solution of NaCl. The organic layer was dried over Na2SO4, filtered and then the filtrate evaporated.

후처리

  1. temperatureunder reflux for 4 hours
  2. distillationwas distilled off in vacuum
  3. dissolutionthe residue dissolved in 100 mL of dry toluene
  4. filtrationThe resulting AgCl precipitate was filtered off through silica
  5. additionthe filtrate was treated with 100 mL of a saturated aqueous solution of sodium bicarbonate
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. customthe filtrate evaporated

출처 및 근거

ORD 기록
ord-e1b73d28aa304de09ead78bae0f1502b
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05612468

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