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

HRID 1981881ノート

反応式

HRID 1981881 の反応式
[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]

参加物

6

反応物 3

HCID 6097028Ammonium SulfateHCID 9975824HCID 9975824、化合物HCID 178509020HCID 178509020、化合物2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 13838Hexamethyldisilazane溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-e24d1fab15e745f09604e096cd265376
出典データセット
uspto-grants-1986_06
特許番号
US04594339

反応ノート

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