Dichloromethane → HCID 68614487, compound

HRID 1244608Notes

Reaction equation

HRID 1244608 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([N:17]3[C:21](=[O:22])[CH2:20][CH:19]([C:23]([OH:25])=[O:24])[CH2:18]3)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.Cl[CH2:27]Cl>CO.S(=O)(=O)(O)O>[CH3:27][O:24][C:23]([CH:19]1[CH2:20][C:21](=[O:22])[N:17]([C:14]2[CH:15]=[CH:16][C:11](/[CH:10]=[CH:9]/[C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[CH:12][CH:13]=2)[CH2:18]1)=[O:25]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 21920058HCID 21920058, compound

Product 1

HCID 68614487HCID 68614487, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 700 mg (2.1 mmol) of (RS)-(E)-1-{4-[2-(4-methoxy-phenyl)-vinyl]-phenyl}-5-oxo-pyrrolidine-3-carboxylic acid in 7 ml of dichloromethane and 0.7 ml of methanol is treated with 1 drop of sulfuric acid and heated at 40° C. for 20 hours. For the working-up, the solvent is evaporated, thereafter, the residue is treated with water and ethyl acetate. The organic layer is separated, dried over magnesium sulfate, and evaporated under reduced pressure. After crystallization from ether of the crude ester, 584 mg (80% of theory) of (RS)-(E)-1-{4-[2-(4-methoxy-phenyl)-vinyl]-phenyl}-5-oxo-pyrrolidine-3-carboxylic acid methyl ester are obtained as a light brown solid; MS: m/e=352 (M+H)+.

Workup

  1. customthe solvent is evaporated
  2. additionthe residue is treated with water and ethyl acetate
  3. customThe organic layer is separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customAfter crystallization from ether of the crude ester, 584 mg (80% of theory) of (RS)-(E)-1-{4-[2-(4-methoxy-phenyl)-vinyl]-phenyl}-5-oxo-pyrrolidine-3-carboxylic acid methyl ester
  7. customare obtained as a light brown solid

Sources & evidence

ORD record
ord-4786d340a99d406e97f9bf16d82ff046
Source dataset
uspto-grants-2006_10
Patent number
US07122562B2

Reaction notes

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