Trityl chloride → 9-(2',3',5'-O-triacetyl-b-D-ribofuranosyl)-2,6-dichloropurine

HRID 248130

反応式

HRID 248130 の反応式
N(OCCCCC)=O.[C:9]([C@@:12]1([OH:37])[C@:16]([C:18](=[O:20])[CH3:19])([OH:17])[C@@H:15]([CH2:21][O:22][C:23](=[O:25])[CH3:24])[O:14][C@H:13]1[N:26]1[CH:34]=[N:33][C:32]2[C:27]1=[N:28][C:29](N)=[N:30][C:31]=2[Cl:35])(=[O:11])[CH3:10].C1(C([Cl:57])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[C:9]([C@@:12]1([OH:37])[C@:16]([C:18](=[O:20])[CH3:19])([OH:17])[C@@H:15]([CH2:21][O:22][C:23](=[O:25])[CH3:24])[O:14][C@H:13]1[N:26]1[CH:34]=[N:33][C:32]2[C:27]1=[N:28][C:29]([Cl:57])=[N:30][C:31]=2[Cl:35])(=[O:11])[CH3:10]

参加物

6

反応物 4

HCID 6456Trityl chlorideHCID 10026Pentyl nitriteHCID 11430Potassium CarbonateHCID 867431892-amino-6-chloro-9-(2,3,5-O-triacetyl-beta-D-ribofuranosyl)-9H-purine

生成物 1

HCID 1317178999-(2',3',5'-O-triacetyl-b-D-ribofuranosyl)-2,6-dichloropurine収率 74.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

n-Pentyl nitrite (98 g, 838 mM) is added over one hour at room temperature under nitrogen to a mixture of the compound of Example 2 (350 g, 819 mM), triphenylmethyl chloride (500 g, 1.79 M) and potassium carbonate (65 g) in CH2Cl2 (3 L). The resulting mixture is heated at reflux for 20 minutes, cooled to room temperature and filtered. The filtrate is concentrated in vacuo, and the resulting residue is purified by column chromatography on silica gel (2.5 kg, ethyl acetate/hexane 1:4-3:7) to yield the title compound as a pale yellow solid (272 g, 74%).

後処理

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for 20 minutes
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe resulting residue is purified by column chromatography on silica gel (2.5 kg, ethyl acetate/hexane 1:4-3:7)

出典と根拠

ORDレコード
ord-7f1279cc1061468d873edb8b1a1305bf
出典データセット
uspto-grants-1993_05
特許番号
US05208327

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