HCID 67771533, compound → HCID 67771360, compound

HRID 1720507Notes

Reaction equation

HRID 1720507 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([O:6][CH2:7][CH:8]([C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15](=[O:31])[C@@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21](=[O:30])[CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[OH:9])=[CH:4][CH:3]=1>CS(C)=O>[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([O:6][CH2:7][C:8]([C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15](=[O:31])[C@@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21](=[O:30])[CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 67771533HCID 67771533, compound

Product 1

HCID 67771360HCID 67771360, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of (2S)-2-[2-(4-chlorophenoxy)-1-hydroxyethyl]-1-[N-(3-phenylpropionyl)-L-prolyl]pyrrolidine (1.59 g) in DMSO (10 ml) was dropwise added a solution of sulfur trioxide-pyridine complex (2.69 g) in DMSO (10 ml), followed by 1 hour's stirring at room temperature. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, saturated aqueous solution of sodium bicarbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluate: chloroform-methanol) to give 0.85 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 1N hydrochloric acid, saturated aqueous solution of sodium bicarbonate and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (eluate: chloroform-methanol)

Sources & evidence

ORD record
ord-f7d01b44148b4c1d917f0a610aea4d61
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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