4-Nitrobenzoyl chloride → HCID 136187746, compound

HRID 635501Notes

Reaction equation

HRID 635501 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].[O:13]([CH2:20][C:21]([NH:23][C:24]1[NH:25][C:26](=[O:41])[C:27]2[N:28]=[CH:29][N:30]([C:39]=2[N:40]=1)[C@@H:31]1[O:38][C@H:35]([CH2:36][OH:37])[C@@H:33]([OH:34])[CH2:32]1)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:37][CH2:36][C@H:35]2[O:38][C@@H:31]([N:30]3[C:39]4[N:40]=[C:24]([NH:23][C:21](=[O:22])[CH2:20][O:13][C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=5)[NH:25][C:26](=[O:41])[C:27]=4[N:28]=[CH:29]3)[CH2:32][C@@H:33]2[OH:34])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 1355299322′-Deoxy-N-(2-phenoxyacetyl)guanosine

Product 1

HCID 136187746HCID 136187746, compound

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-phenoxyacetyldeoxyguanosine for 16 hours in pyridine. After extraction with a dichloromethane/sodium bicarbonate mixture and evaporation to dryness, the product is taken up in chloroform and purified on a silica column (elution 4% methanol). The product is only slightly soluble in organic solvents.

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
  5. custompurified on a silica column (elution 4% methanol)

Sources & evidence

ORD record
ord-8e38cd4cc07e49aa8bbe3516d4e4477d
Source dataset
uspto-grants-2001_02
Patent number
US06187914B1

Reaction notes

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