Palmitoyl chloride → 5'-O-palmitoyl-N2-isobutyryl-2'-deoxyguanosine

HRID 969772Notes

Reaction equation

HRID 969772 reaction equation
[C:1]([NH:6][C:7]1[NH:8][C:9](=[O:24])[C:10]2[N:11]=[CH:12][N:13]([C:22]=2[N:23]=1)[C@@H:14]1[O:21][C@H:18]([CH2:19][OH:20])[C@@H:16]([OH:17])[CH2:15]1)(=[O:5])[CH:2]([CH3:4])[CH3:3].CC(N(C)C)=O.[C:31](Cl)(=[O:47])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46].C(=O)(O)[O-].[K+]>N1C=CC=CC=1>[C:31]([O:20][CH2:19][C@H:18]1[O:21][C@@H:14]([N:13]2[C:22]3[N:23]=[C:7]([NH:6][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[NH:8][C:9](=[O:24])[C:10]=3[N:11]=[CH:12]2)[CH2:15][C@@H:16]1[OH:17])(=[O:47])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]

Participants

6

Reactant 4

HCID 8206Palmitoyl chlorideHCID 31374DimethylacetamideHCID 516893Potassium BicarbonateHCID 135407017Guanosine, 2'-deoxy-N-(2-methyl-1-oxopropyl)-

Product 1

HCID 1361079535'-O-palmitoyl-N2-isobutyryl-2'-deoxyguanosine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

To an oven-dried 100 mL round-bottomed flask containing a stir bar was added N2-isobutyryl-2′-deoxyguanosine (0.75 g, 1 eq.). The flask was fitted with a septum and dry dimethylacetamide (DMA, 32 mL) and dry pyridine (16 mL) were added via cannula, with swirling and stirring. The flask was purged with argon gas, the slurry was allowed to cool 10 min. in an ice bath, and palmitoyl chloride (2.5 eq.) was added dropwise over 5 min. The mixture was allowed to stir while it slowly warmed to 25° C. After 24 h, the mixture was poured into 200 mL of 0.5 M potassium bicarbonate solution giving a white solid which was isolated by suction filtration, washed with 3×30 mL H2O, air dried, and finally dried under high vacuum giving a white powder. This crude product was purified by flash chromatography (silica gel bed, eluted with chloroform-methanol) giving a white powder. 1H-NMR and elemental analysis data were consistent with the assigned structure.

Workup

  1. additionTo an oven-dried 100 mL round-bottomed flask containing a stir bar
  2. additionwere added via cannula
  3. customThe flask was purged with argon gas
  4. temperatureto cool 10 min. in an ice bath
  5. stirringto stir while it
  6. customgiving a white solid which
  7. customwas isolated by suction filtration
  8. washwashed with 3×30 mL H2O, air
  9. customdried
  10. customfinally dried under high vacuum
  11. customgiving a white powder
  12. customThis crude product was purified by flash chromatography (silica gel bed, eluted with chloroform-methanol)
  13. customgiving a white powder

Sources & evidence

ORD record
ord-7f08c8b0348e4d57a21551a69578245f
Source dataset
uspto-grants-2007_12
Patent number
US07307166B1

Reaction notes

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