Dichloromethane → HCID 70456614, compound

HRID 1380037Notes

Reaction equation

HRID 1380037 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[N:9]=[CH:8][N:7]([CH2:13][O:14][CH:15]([CH2:18][OH:19])[CH2:16][OH:17])[C:6]=2[N:5]=[C:3]1[NH2:4].[C:20](Cl)(=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(Cl)Cl>CN(C=O)C>[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[N:9]=[CH:8][N:7]([CH2:13][O:14][CH:15]([CH2:18][O:19][C:20](=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:16][O:17][C:20](=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:6]=2[N:5]=[C:3]1[NH2:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8124Octanoyl chlorideHCID 13606738HCID 13606738, compound

Product 1

HCID 70456614HCID 70456614, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1-Methyl-9-(1,3-dihydroxy-2-propoxymethyl) guanine (340 mg, 1.26 mmol) was suspended in dry DMF and dry pyridine (approximately 20 ml total) and evaporated to dryness. This process was repeated twice, the final time concentrating the suspension down to 10 ml. This suspension was cooled to 0°, under N2, and a solution of octanoyl chloride (822 mg, 5.05 mmol) in dry DMF (1 ml) was added. This reaction was stirred overnight at room temperature. Methylene chloride was then added and the mixture was extracted with saturated aqueous NaHCO3 solution. The organic phase was then washed three times with H2O, dried over MgSO4, filtered and evaporated to dryness. The residual oil was dissolved in CH2Cl2 and applied to a column of silica gel, packed in CH2Cl2. Elution was first performed with CH2Cl2 followed by 1% MeOH in CH2Cl2 (200 ml), 2% MeOH in CH2Cl2 (200 ml), 3% MeOH in CH2Cl2 (100 ml) and finally 5% MeOH in CH2Cl2 (100 ml). Fractions containing the required product were pooled and evaporated to dryness to give 529 mg of product. It was recrystallized from ether/petroleum ether. The PMR spectrum was in accord with the structure.

Workup

  1. customdry pyridine (approximately 20 ml total) and evaporated to dryness
  2. concentrationthe final time concentrating the suspension down to 10 ml
  3. temperatureThis suspension was cooled to 0°, under N2
  4. extractionthe mixture was extracted with saturated aqueous NaHCO3 solution
  5. washThe organic phase was then washed three times with H2O
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. dissolutionThe residual oil was dissolved in CH2Cl2
  10. washElution
  11. additionFractions containing the required product
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-6ccddf08caf44963b33f6123b284ab2d
Source dataset
uspto-grants-1986_04
Patent number
US04579849

Reaction notes

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