N3-[2-(2-nitrophenyl)propoxycarbonyl]-N-methyl imidazolium chloride → N4-((4-tertbutylphenoxy)acetyl)-3'-O-[2-(2-nitrophenyl)propoxycarbonyl]-2'-deoxycytidine

HRID 354214Notes

Reaction equation

HRID 354214 reaction equation
[C:1]([C:5]1[CH:30]=[CH:29][C:8]([O:9][CH2:10][C:11]([NH:13][C:14]2[CH:27]=[CH:26][N:17]([C@@H:18]3[O:25][C@H:22]([CH2:23][OH:24])[C@@H:20]([OH:21])[CH2:19]3)[C:16](=[O:28])[N:15]=2)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[N+:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[CH:41]([CH3:52])[CH2:42][O:43][C:44](N1C=C[N+](C)=C1)=[O:45])([O-:34])=[O:33]>ClCCl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]([NH:13][C:14]2[CH:27]=[CH:26][N:17]([C@@H:18]3[O:25][C@H:22]([CH2:23][OH:24])[C@@H:20]([O:21][C:44]([O:43][CH2:42][CH:41]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=4[N+:32]([O-:34])=[O:33])[CH3:52])=[O:45])[CH2:19]3)[C:16](=[O:28])[N:15]=2)=[O:12])=[CH:29][CH:30]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 11232610N3-[2-(2-nitrophenyl)propoxycarbonyl]-N-methyl imidazolium chlorideHCID 69929427N4-((4-tertbutylphenoxy)acetyl)-2'-deoxycytidine

Product 1

HCID 15539315N4-((4-tertbutylphenoxy)acetyl)-3'-O-[2-(2-nitrophenyl)propoxycarbonyl]-2'-deoxycytidineYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

As described for 11 with N4-((4-tertbutylphenoxy)acetyl)-2′-deoxycytidine (4) (5 g, 6.93 mmol) in 50 ml dichloromethane and 2 (2.71 g, 8.32 mmol) in 50 ml dichloromethane. Purification by precipitation using toluene yielded 3.16 g (73%) of the title compound.

Workup

  1. customPurification
  2. customby precipitation

Sources & evidence

ORD record
ord-0686aa28e39c4a06b8aa3c59b0a97bb7
Source dataset
uspto-grants-2004_06
Patent number
US06756492B1

Reaction notes

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