N3-[2-(2-nitrophenyl)propoxycarbonyl]-N-methyl imidazolium chloride → HCID 136388380, compound

HRID 354215Notes

Reaction equation

HRID 354215 reaction equation
[C:1]([C:5]1[CH:33]=[CH:32][C:8]([O:9][CH2:10][C:11]([NH:13][C:14]2[NH:15][C:16](=[O:31])[C:17]3[N:18]=[CH:19][N:20]([C:29]=3[N:30]=2)[C@@H:21]2[O:28][C@H:25]([CH2:26][OH:27])[C@@H:23]([OH:24])[CH2:22]2)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[N+:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[CH:44]([CH3:55])[CH2:45][O:46][C:47](N1C=C[N+](C)=C1)=[O:48])([O-:37])=[O:36]>ClCCl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]([NH:13][C:14]2[NH:15][C:16](=[O:31])[C:17]3[N:18]=[CH:19][N:20]([C:29]=3[N:30]=2)[C@@H:21]2[O:28][C@H:25]([CH2:26][OH:27])[C@@H:23]([O:24][C:47]([O:46][CH2:45][CH:44]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=3[N+:35]([O-:37])=[O:36])[CH3:55])=[O:48])[CH2:22]2)=[O:12])=[CH:32][CH:33]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 11232610N3-[2-(2-nitrophenyl)propoxycarbonyl]-N-methyl imidazolium chlorideHCID 1361160972-(4-(tert-Butyl)phenoxy)-N-(9-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide

Product 1

HCID 136388380HCID 136388380, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

As described for 11 with N2-((4-tertbutylphenoxy)acetyl)-2′-deoxyguanosine (6) (5 g, 6.58 mmol) in 50 ml dichloromethane and 2 (2.57 g, 7.9 mmol) in 50 ml dichloromethane. Purification via flash chromatography (0-10% methanol in toluene/ethyl acetate (1:1) yielded 3.53 g (81%) of the title compound.

Workup

  1. customPurification via flash chromatography (0-10% methanol in toluene/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-4170e30dda0e41519b70c8fa1b39dae0
Source dataset
uspto-grants-2004_06
Patent number
US06756492B1

Reaction notes

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