Oxalyl chloride → N6-(Benzyloxycarbonyl)-9-(chlorocarbonylmethyl)adenine

HRID 343985Notes

Reaction equation

HRID 343985 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH2:7]([O:14][C:15]([NH:17][C:18]1[N:26]=[CH:25][N:24]=[C:23]2[C:19]=1[N:20]=[CH:21][N:22]2CC(O)=O)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>ClCCl>[CH2:7]([O:14][C:15]([NH:17][C:18]1[N:26]=[CH:25][N:24]=[C:23]2[C:19]=1[N:20]=[CH:21][N:22]2[CH2:1][C:2]([Cl:4])=[O:3])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 154805149H-Purine-9-acetic acid, 6-[[(phenylmethoxy)carbonyl]amino]-

Product 1

HCID 22014446N6-(Benzyloxycarbonyl)-9-(chlorocarbonylmethyl)adenine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (6.3 g, 50 mmol) is added dropwise over 5 minutes to a solution of N6 -(benzyloxycarbonyl)-9-(carboxymethyl)adenine (16.6 g, 50 mmol) dissolved in dichloromethane (200 mL). The reaction is stirred until gas evolution has ceased and then for an additional 2 hours. The reaction mixture is evaporated to an oil.

Workup

  1. customThe reaction mixture is evaporated to an oil

Sources & evidence

ORD record
ord-0b80d97dbda74bd4af42ad0952b4d79a
Source dataset
uspto-grants-1999_01
Patent number
US05864010

Reaction notes

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