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

HRID 248130

반응식

HRID 248130 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-7f1279cc1061468d873edb8b1a1305bf
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05208327

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