Methanol → HCID 19871299, compound

HRID 329685Notes

Reaction equation

HRID 329685 reaction equation
[N:1]([CH2:4][C:5]([OH:34])([CH3:33])[CH2:6][O:7][CH2:8][C:9]1[NH:10][C:11]([CH3:32])=[C:12]([C:28]([O:30][CH3:31])=[O:29])[CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=2[Cl:27])[C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N+]=[N-].C(S)CCS.C(N(CC)CC)C.C[OH:48]>>[C:8]([OH:7])(=[O:48])/[CH:9]=[CH:14]/[C:15]([OH:17])=[O:16].[NH2:1][CH2:4][C:5]([OH:34])([CH3:33])[CH2:6][O:7][CH2:8][C:9]1[NH:10][C:11]([CH3:32])=[C:12]([C:28]([O:30][CH3:31])=[O:29])[CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=2[Cl:27])[C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 4

HCID 887MethanolHCID 80131,3-PropanedithiolHCID 8471TriethylamineHCID 14810602HCID 14810602, compound

Product 1

HCID 19871299HCID 19871299, compound

Procedure

A solution of 1-azido-3-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}-2-hydroxy-2-methylpropane (1.54 g), propane-1,3-dithiol (1.2 ml) and triethylamine (1.7 ml) in methanol (30 ml) was stirred at room temperature for eight days, filtered and evaporated. The residue was partitioned between ethyl acetate and water and the layers separated. The organic layer was washed with water, dried over Na2SO4 and evaporated. The residue was purified by chromatography on SiO2 (15 g) using dichloromethane plus 0-40% methanol as the eluant. Appropriate fractions were combined and evaporated. The residue was taken up in ethyl acetate and the solution was treated with excess fumaric acid. The resulting solid was collected, washed with ethyl acetate and dried to give the title compound (0.49 g), m.p. 110°-115° C.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customThe residue was partitioned between ethyl acetate and water
  4. customthe layers separated
  5. washThe organic layer was washed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe residue was purified by chromatography on SiO2 (15 g)
  9. customevaporated
  10. additionthe solution was treated with excess fumaric acid
  11. customThe resulting solid was collected
  12. washwashed with ethyl acetate
  13. customdried

Sources & evidence

ORD record
ord-5d5d4f0cd2584f5e8d854b43c91a40df
Source dataset
uspto-grants-1990_01
Patent number
US04892881

Reaction notes

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