Ammonium Sulfate → 1-(3-O-Acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-4-amino-5-chloro-2(1H)-pyrimidinone

HRID 1981881노트

반응식

HRID 1981881 반응식
[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:8][CH:7](Br)[C@H:6]1[F:21])(=[O:3])[CH3:2].[Cl:22][C:23]1[C:24]([NH2:30])=[N:25][C:26](=[O:29])[NH:27][CH:28]=1.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>C(Cl)Cl.C[Si](C)(C)N[Si](C)(C)C>[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:8][C@@H:7]([N:27]2[CH:28]=[C:23]([Cl:22])[C:24]([NH2:30])=[N:25][C:26]2=[O:29])[C@H:6]1[F:21])(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 6097028Ammonium SulfateHCID 9975824HCID 9975824, 화합물HCID 178509020HCID 178509020, 화합물2회

생성물 1

HCID 542677591-(3-O-Acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-4-amino-5-chloro-2(1H)-pyrimidinone

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 13838Hexamethyldisilazane용매

실험 절차

To a solution of 3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide (3.6 g, 0.01 mol) in methylene chloride (50 ml) is added a methylene chloride solution of 5-chloro-tris(trimethylsilyl)cystosine [prepared from 4.3 g, 0.03 mol. of 5-chlorocytosine as follows: a mixture of 5-chlorocytosine and 5-15 mg of ammonium sulfate in 43 ml of hexamethyldisilazane is heated to reflux until a clear solution is obtained. The excess hexamethyldisilazane is removed by evaporation in vacuo and the residue is dissolved in 25 ml of methylene chloride]. The mixture is stirred for 5 days at room temperature. Methanol (7 ml) is added to the reaction mixture, and the suspension is filtered through a Celite pad which is thoroughly washed with methylene chloride. The combined filtrate and washings are evaporated to dryness in vacuo and the residue is crystallized from ethanol to give 860 mg of 1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-chlorocytosine, m.p. 233°.

후처리

  1. customprepared from 4.3 g, 0.03 mol
  2. temperatureis heated
  3. temperatureto reflux until a clear solution
  4. customis obtained
  5. customThe excess hexamethyldisilazane is removed by evaporation in vacuo
  6. dissolutionthe residue is dissolved in 25 ml of methylene chloride]
  7. additionMethanol (7 ml) is added to the reaction mixture
  8. filtrationthe suspension is filtered through a Celite pad which
  9. washis thoroughly washed with methylene chloride
  10. customThe combined filtrate and washings are evaporated to dryness in vacuo
  11. customthe residue is crystallized from ethanol

출처 및 근거

ORD 기록
ord-e24d1fab15e745f09604e096cd265376
출처 데이터셋
uspto-grants-1986_06
특허 번호
US04594339

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