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

HRID 248130

Reaction equation

HRID 248130 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-7f1279cc1061468d873edb8b1a1305bf
Source dataset
uspto-grants-1993_05
Patent number
US05208327

Linked notes

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