Water → HCID 178494609, compound

HRID 235975Notes

Reaction equation

HRID 235975 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:11][CH:12]=[C:13]([CH2:15][O:16][CH3:17])[N:14]=2)=[CH:6][CH:5]=1.CS(O)(=O)=O.CC1(C)[O:28][CH:27]([CH2:29]O)[CH2:26][O:25]1.O>CN(C=O)C>[CH3:17][O:16][CH2:15][C:13]1[N:14]=[C:10]([C:7]2[CH:6]=[CH:5][C:4]([O:3][CH2:29][CH:27]([OH:28])[CH2:26][OH:25])=[CH:9][CH:8]=2)[NH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 76519763HCID 76519763, compoundHCID 178494607HCID 178494607, compound

Product 1

HCID 178494609HCID 178494609, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

Under N2, a mixture of NaH (1.5 g, 0.037 mol), 60% oil dispersion), DMF (45 mol) and 89 (6.8 g, 0.033 mol) was heated at 80° C. for 30 minutes and then a solution of 2,2-dimethyl-4-(hydroxymethyl)-1,3-dioxolane methansulfonate (8.4 g, 0.04 mol) in DMF (25 ml) was added dropwise. After the addition, the mixture was heated at 120° C. with stirring for 18 hours. The mixture was then poured into H2O and the solution extracted with EtOAc (4×). The combined organic extracts were backwashed with H2O, 5% NaOH, dried, filtered and concentrated to dryness. The residue was combined with acetone (75 ml) and 3N HCl (75 ml) and the solution heated on a steam bath for 30 minutes. After cooling, the solution was adjusted to pH 10 and extracted with 10% CH3OH--CHCl3. The combined extracts were dried, filtered and concentrated to dryness. The residue was chromatographed on silica gel and the product eluted with 10% CH3OH--CHCl3 to yield 1.7 g of 90 (18%); m.p. 154°-56° C. (isoProOH).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated at 120° C.
  3. extractionthe solution extracted with EtOAc (4×)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. temperaturethe solution heated on a steam bath for 30 minutes
  8. temperatureAfter cooling
  9. extractionextracted with 10% CH3OH
  10. customThe combined extracts were dried
  11. filtrationfiltered
  12. concentrationconcentrated to dryness
  13. customThe residue was chromatographed on silica gel
  14. washthe product eluted with 10% CH3OH

Sources & evidence

ORD record
ord-7fc57f0cfc8448ce97b011dfa7a7c2e2
Source dataset
uspto-grants-1987_02
Patent number
US04642311

Reaction notes

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