Water → HCID 73654867, compound

HRID 1086591Notes

Reaction equation

HRID 1086591 reaction equation
[I-].[Na+].[CH:3]([NH:5][C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:7][C:8](=C)[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:4].O>C(COC)OC.[Zn]>[CH:3]([NH:5][C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:7]=[CH:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:4]

Participants

6

Reactant 3

HCID 962Water2×HCID 5238Sodium IodideHCID 14407403HCID 14407403, compound

Product 1

HCID 73654867HCID 73654867, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

4.2 g of sodium iodide and 3.7 g of zinc were added to a solution of 2.4 g of the product A of Step C of Example 1 and the reaction medium in dimethoxyethane was refluxed in the presence of water with stirring for 2 hours. 50 ml of water were added and after filtration, extraction was carried out with methylene chloride. The extracts were dried and evaporated to dryness under reduced pressure to obtain 2.3 g of crude product which was chromatographed on silica. Elution with a cyclohexane ethyl acetate mixture (5-5) yielded 1.6 g of the expected product.

Workup

  1. filtrationafter filtration, extraction
  2. customThe extracts were dried
  3. customevaporated to dryness under reduced pressure
  4. customto obtain 2.3 g of crude product which
  5. customwas chromatographed on silica
  6. washElution with a cyclohexane ethyl acetate mixture (5-5)

Sources & evidence

ORD record
ord-72b07527c4ba4f1bb1f00c5c73d016f6
Source dataset
uspto-grants-1991_07
Patent number
US05030715

Reaction notes

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