Triacetoxyperiodinane → 2-acetyl-9-[2-chloro-4-ethoxycarbonylmethoxy-5-(2,3-difluoro-6-methoxybenzyloxy)phenyl]-6-methoxy-7,9-dihydro-8H-purin-8-one

HRID 1513071Notes

Reaction equation

HRID 1513071 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:15][CH2:16][C:17]2[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[C:19]([F:25])[C:18]=2[F:26])=[CH:4][C:3]=1[N:27]1[C:35](=[O:36])[NH:34][C:33]2[C:28]1=[N:29][C:30]([CH:39]([OH:41])[CH3:40])=[N:31][C:32]=2[O:37][CH3:38].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C(Cl)Cl>[C:39]([C:30]1[N:29]=[C:28]2[C:33]([NH:34][C:35](=[O:36])[N:27]2[C:3]2[CH:4]=[C:5]([O:15][CH2:16][C:17]3[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[C:19]([F:25])[C:18]=3[F:26])[C:6]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:7][C:2]=2[Cl:1])=[C:32]([O:37][CH3:38])[N:31]=1)(=[O:41])[CH3:40]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59309873HCID 59309873, compound

Product 1

HCID 593101042-acetyl-9-[2-chloro-4-ethoxycarbonylmethoxy-5-(2,3-difluoro-6-methoxybenzyloxy)phenyl]-6-methoxy-7,9-dihydro-8H-purin-8-oneYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9-[2-chloro-4-ethoxycarbonylmethoxy-5-(2,3-difluoro-6-methoxy-benzyloxy)phenyl]-2-(1-hydroxyethyl)-6-methoxy-7,9-dihydro-8H-purin-8-one (0.17 g) in methylene chloride (3 mL) was added 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one (0.37 g), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1−1/6) to give the title compound (0.1 g)

Workup

  1. customThe reaction mixture was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1−1/6)

Sources & evidence

ORD record
ord-99ac60a72eac488098cd8fdc85e9a9f0
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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