4-Nitrobenzoyl chloride → 5'-o-p-Nitrobenzoyl-6-n-phenoxyacetyldeoxyadenosine

HRID 635498Notes

Reaction equation

HRID 635498 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[C:25]2[N:26]=[CH:27][N:28]([C:37]=2[N:38]=[CH:39][N:40]=1)[C@@H:29]1[O:36][C@H:33]([CH2:34][OH:35])[C@@H:31]([OH:32])[CH2:30]1)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:35][CH2:34][C@H:33]2[O:36][C@@H:29]([N:28]3[C:37]4[N:38]=[CH:39][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)[C:25]=4[N:26]=[CH:27]3)[CH2:30][C@@H:31]2[OH:32])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 85024-Nitrobenzoyl chlorideHCID 105241302'-Deoxy-N6-phenoxyacetyladenosineHCID 86584982Sodium bicarbonate ethyl acetate

Product 1

HCID 153826945'-o-p-Nitrobenzoyl-6-n-phenoxyacetyldeoxyadenosine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

The synthesis of this product is carried out by reacting 1.1 eq of p-nitrobenzoyl chloride with 6-N-phenoxyacetyldeoxyadenosine for 4 hours in pyridine. After hydrolysis of the excess reagent, almost complete evaporation of the pyridine, and ethyl acetate/sodium bicarbonate extraction, the ethyl acetate phase is evaporated to dryness. The product is obtained by column chromatography with a gradient of methanol in chloroform (elution 4% methanol).

Workup

  1. customThe synthesis of this product
  2. customfor 4 hours
  3. customthe ethyl acetate phase is evaporated to dryness
  4. customThe product is obtained by column chromatography with a gradient of methanol in chloroform (elution 4% methanol)

Sources & evidence

ORD record
ord-70f62e679ece4c38a1b08c7a43c9e407
Source dataset
uspto-grants-2001_02
Patent number
US06187914B1

Reaction notes

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