Water → HCID 86656664, compound

HRID 882929Notes

Reaction equation

HRID 882929 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH:5]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([S:20](O)(=[O:22])=[O:21])[CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O=P(Cl)(Cl)[Cl:27].N1C=CC=CC=1.O>CN1CCN(C)C1=O>[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH:5]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([S:20]([Cl:27])(=[O:22])=[O:21])[CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 86656663HCID 86656663, compound

Product 1

HCID 86656664HCID 86656664, compound

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Procedure

To a solution of 3-(4-methoxy-3-sulfo-phenyl)-3-phenyl-propionic acid methyl ester (850 mg, 2.43 mmol) in 1,3-dimethyl-2-imidazolidinone (25 mL) is added POCl3 (0.57 ml, 6.06 mmol) and pyridine (0.33 mL, 4.13 mmol). The reaction mixture is stirred at RT for 1 h. After this time, water (50 mL) is added and the reaction mixture is extracted with DCM (3×50 mL). The combined organic phases are washed with brine (30 mL) then dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as an oil.

Workup

  1. extractionthe reaction mixture is extracted with DCM (3×50 mL)
  2. washThe combined organic phases are washed with brine (30 mL)
  3. dry with materialthen dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c4dca733343a4edaa34064a29ce6e605
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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