4-Nitrobenzoyl chloride → 5'-O-p-Nitrobenzoyl-2-N-t-Butylphenoxyacetyldeoxyguanosine

HRID 635503Notes

Reaction equation

HRID 635503 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13]([NH:17][C:18]1[NH:19][C:20](=[O:45])[C:21]2[N:22]=[CH:23][N:24]([C:43]=2[N:44]=1)[C@:25]1([C:33](=[O:42])[CH2:34][O:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[O:32][C@H:29]([CH2:30][OH:31])[C@@H:27]([OH:28])[CH2:26]1)([CH3:16])([CH3:15])[CH3:14]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:31][CH2:30][C@H:29]2[O:32][C@@:25]([C:33](=[O:42])[CH2:34][O:35][C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)([N:24]3[C:43]4[N:44]=[C:18]([NH:17][C:13]([CH3:14])([CH3:16])[CH3:15])[NH:19][C:20](=[O:45])[C:21]=4[N:22]=[CH:23]3)[CH2:26][C@@H:27]2[OH:28])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 1364767972-N-t-butylphenoxyacetyldeoxyguanosine

Product 1

HCID 1371829655'-O-p-Nitrobenzoyl-2-N-t-Butylphenoxyacetyldeoxyguanosine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The synthesis of this product is carried out by reacting 1.1 eq of p-nitrobenzoyl chloride with 2-N-t-butylphenoxyacetyldeoxyguanosine for 16 hours in pyridine. After extraction with a dichloromethane/methanol mixture and evaporation to dryness, the product is taken up in chloroform/hexane (8/2) and purified on a silica column (elution 3% methanol). The product obtained is very soluble in organic solvents.

Workup

  1. customThe synthesis of this product
  2. customfor 16 hours
  3. extractionAfter extraction
  4. customwith a dichloromethane/methanol mixture and evaporation to dryness
  5. custompurified on a silica column (elution 3% methanol)
  6. customThe product obtained

Sources & evidence

ORD record
ord-11c8a64b24de4a72bee26fc3b2d98780
Source dataset
uspto-grants-2001_02
Patent number
US06187914B1

Reaction notes

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