HCID 14810587, compound → HCID 88616475, compound

HRID 569589Notes

Reaction equation

HRID 569589 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][CH:23]2[CH2:27][O:26]C(C)(C)[O:24]2)=[C:10]1[C:30]([O:32][CH2:33][CH3:34])=[O:31]>C(O)(=O)C>[OH2:16].[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][CH:23]([OH:24])[CH2:27][OH:26])=[C:10]1[C:30]([O:32][CH2:33][CH3:34])=[O:31].[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][CH:23]([OH:24])[CH2:27][OH:26])=[C:10]1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

3

Reactant 1

HCID 14810587HCID 14810587, compound

Product 1

HCID 88616475HCID 88616475, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxymethyl}-2,2-dimethyl-1,3-dioxolane (5.9 g) in 60% aqueous acetic acid was stirred at room temperature for 27 hours and then evaporated. The residue was partitioned between ethyl acetate and water and the organic layer was washed with water, dried over Na2SO4 and evaporated. The residue was purified by chromatography on SiO2 (60 g) using toluene plus 0-100% ethyl acetate as the eluant. Appropriate fractions were combined and evaporated and the residue crystallised from ether to give the title compound (2.3 g) as a hemihydrate, m.p. 115°-120° C.

Workup

  1. customevaporated
  2. customThe residue was partitioned between ethyl acetate and water
  3. washthe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by chromatography on SiO2 (60 g)
  7. customevaporated
  8. customthe residue crystallised from ether

Sources & evidence

ORD record
ord-c10f67b9818448c184ff4f79106e32ab
Source dataset
uspto-grants-1988_03
Patent number
US04732985

Reaction notes

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