4-Nitrobenzoyl chloride → 5'-O-p-Nitrobenzoyl-2-N-Isobutyryldeoxyguanosine

HRID 635500Notes

Reaction equation

HRID 635500 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:18][C:19]1[NH:20][C:21](=[O:36])[C:22]2[N:23]=[CH:24][N:25]([C:34]=2[N:35]=1)[C@@H:26]1[O:33][C@H:30]([CH2:31][OH:32])[C@@H:28]([OH:29])[CH2:27]1)(=[O:17])[CH:14]([CH3:16])[CH3:15]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:32][CH2:31][C@H:30]2[O:33][C@@H:26]([N:25]3[C:34]4[N:35]=[C:19]([NH:18][C:13](=[O:17])[CH:14]([CH3:15])[CH3:16])[NH:20][C:21](=[O:36])[C:22]=4[N:23]=[CH:24]3)[CH2:27][C@@H:28]2[OH:29])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 135407017Guanosine, 2'-deoxy-N-(2-methyl-1-oxopropyl)-

Product 1

HCID 1371829645'-O-p-Nitrobenzoyl-2-N-Isobutyryldeoxyguanosine

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-isobutyryldeoxyguanosine for 16 hours in pyridine. After extraction with a dichloromethane/sodium bicarbonate mixture and evaporation to dryness, the product is taken up in chloroform. This product was not used because it was too insoluble.

Workup

  1. customThe synthesis of this product
  2. customfor 16 hours
  3. extractionAfter extraction
  4. customwith a dichloromethane/sodium bicarbonate mixture and evaporation to dryness

Sources & evidence

ORD record
ord-9a69e84c0a0941aaba3f666c4f9434bd
Source dataset
uspto-grants-2001_02
Patent number
US06187914B1

Reaction notes

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