Sodium Iodide → HCID 54567442, compound

HRID 439573Notes

Reaction equation

HRID 439573 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([OH:13])[C:10]([O-:12])=[O:11])=[CH:4][CH:3]=1.Cl[CH2:15][CH2:16][O:17][CH2:18][CH2:19]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.O>[OH:13][C@H:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([N:1]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:7][CH:6]=1)[C:10]([O:12][CH2:8][C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)=[O:11]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8115Bis(2-chloroethyl) etherHCID 11430Potassium CarbonateHCID 19036796HCID 19036796, compound

Product 1

HCID 54567442HCID 54567442, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The suspended solution of benzyl R)-3-(4-aminophenyl)-2-hydroxypropionate (0.27 g), bis(2-chloroethyl)ether (0.12 ml), potassium carbonate (0.28 g), and sodium iodide (0.075 g) in dimethylformamide (1 ml) were heated at 70°-90° C. for 7 hours. After cooling it down to room temperature, water (50 ml) was added and extracted with ether (25 ml×3). After the ether layer was washed with saturated brine, it was dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo, the resultant crude product was purified by silica gel column chromatography, and eluted with mixture of hexane, ethyl acetate and ethanol (60:35:5, v/v). The fractions containing the desired product were combined and evaporated in vacuo to obtain benzyl (R)-2-hydroxy-3-(4-morpholinophenyl)propionate (0.14 g)

Workup

  1. extractionextracted with ether (25 ml×3)
  2. washAfter the ether layer was washed with saturated brine, it
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe resultant crude product was purified by silica gel column chromatography
  6. washeluted with mixture of hexane, ethyl acetate and ethanol (60:35:5
  7. additionThe fractions containing the desired product
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-a847d85886764feebdf5f43f944250e1
Source dataset
uspto-grants-1996_05
Patent number
US05514773

Reaction notes

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