Potassium Carbonate → Ethyl 3-{4-chloro-3-[(2S)-oxiran-2-yl]phenyl}propanoate

HRID 602064Notes

Reaction equation

HRID 602064 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][C:3]=1[C@H:15]([OH:28])[CH2:16]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][C:3]=1[C@H:15]1[CH2:16][O:28]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57470611Ethyl 3-[4-chloro-3-((1S)-1-hydroxy-2-{[(4-methylphenyl)sulfonyl]oxy}ethyl)phenyl]propanoate

Product 1

HCID 57470610Ethyl 3-{4-chloro-3-[(2S)-oxiran-2-yl]phenyl}propanoateYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-[4-chloro-3-((1S)-1-hydroxy-2-{[(4-methylphenyl) sulfonyl]oxy}ethyl)phenyl]propanoate (1.77 g, 4.1 mmol) in absolute ethanol (12 mL) was added potassium carbonate (0.63 g, 4.6 mmol) and the reaction was stirred at rt for 3 days. The reaction was concentrated and diluted with water and extracted with EtOAc (2×). The combined organic layers were washed with H2O, brine, dried (Na2SO4), and concentrated to afford 810 mg of product as a white solid (78%). The product was pure enough to use in the subsequent step. 1H NMR (400 MHz, chloroform-d) δ ppm 7.27 (d, J=8.59 Hz, 1 H) 7.07-7.10 (m, J=2.72, 2.72, 2.72, 2.72 Hz, 2 H) 4.19 (dd, J=4.04, 2.53 Hz, 1 H) 4.13 (q, J=7.07 Hz, 2 H) 3.19 (dd, J=5.68, 4.17 Hz, 1 H) 2.91 (t, J=7.71 Hz, 2 H) 2.65 (dd, J=5.56, 2.53 Hz, 1 H) 2.59 (t, J=7.58 Hz, 2 H) 1.24 (t, J=7.20 Hz, 3 H)

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with water
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic layers were washed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e8b7c5ea3fe249b693b5aab6c15c83fb
Source dataset
uspto-grants-2011_03
Patent number
US07902394B2

Reaction notes

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