Water → HCID 67524594, compound

HRID 898849Notes

Reaction equation

HRID 898849 reaction equation
[C:1](#[N:3])[CH3:2].[OH2:4].[C:5]([OH:8])(=O)C.[C:9](O)(=O)[CH3:10].I[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:20]([O:23][CH2:24][CH3:25])(=[O:22])C>>[CH3:5][O:8][C:2]([C@@:1]12[CH2:10][C@:9]1([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:25][CH2:24][O:23][C:20](=[O:22])[NH:3]2)=[O:4]

Participants

5

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 12217721Iodo benzene diacetate2×

Product 1

HCID 67524594HCID 67524594, compoundYield 35%

Procedure

To a solution of (1R*,2S*)-cis-1-carbamoyl-2-(2-hydroxyethyl)-2-phenylcyclopropanecarboxylic acid methyl ester (0.30 g, 1.1 mmol) obtained in Preparation Example 2-4-2 in an ethyl acetate:acetonitrile:water=1:2:1 mixture (12 mL) was added iodobenzene diacetate (0.48 g, 1.5 mmol) at 0° C. After stirring at room temperature for 1.5 hours, iodobenzene diacetate (64 mg, 0.23 mmol) was further added, and the mixture was stirred for 1.5 hours. After the obtained solution was diluted with ethyl acetate and separated into layers, the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride solution, and dried over sodium sulfate. After filtration and evaporation, the obtained residue was separated and purified by silica gel chromatography (hexane:ethyl acetate=40:1 to 1:2) to give the title compound (0.11 g, 35%) as a white solid.

Workup

  1. stirringthe mixture was stirred for 1.5 hours
  2. customseparated into layers
  3. extractionthe aqueous layer was extracted twice with ethyl acetate
  4. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration and evaporation
  7. customthe obtained residue was separated
  8. custompurified by silica gel chromatography (hexane:ethyl acetate=40:1 to 1:2)

Sources & evidence

ORD record
ord-ee1ff9789aa24e6a91b784dad53a7629
Source dataset
uspto-grants-2008_04
Patent number
US07351825B2

Reaction notes

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