Pyridine → (2S)-2-(Phenoxyacetyl)-1-[N-(phenoxyacetyl)-L-prolyl]pyrrolidine

HRID 1720531Notes

Reaction equation

HRID 1720531 reaction equation
[OH:1][CH:2]([C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:32])[C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1[C:22](=[O:31])[CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.N1C=CC=CC=1.FC(F)(F)C(O)=O.C1CCC(N=C=NC2CCCCC2)CC1>CS(C)=O.C1C=CC=CC=1>[O:4]([CH2:3][C:2]([C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:32])[C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1[C:22](=[O:31])[CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:1])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 67771420(2S)-2-(1-Hydroxy-2-phenoxyethyl)-1-[N-(phenoxyacetyl)-L-prolyl]pyrrolidin

Product 1

HCID 67771029(2S)-2-(Phenoxyacetyl)-1-[N-(phenoxyacetyl)-L-prolyl]pyrrolidineYield 76.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

(2S)-2-(1-Hydroxy-2-phenoxyethyl)-1-[N-(phenoxyacetyl)-L-prolyl]pyrrolidine (998 mg) was dissolved in a mixture of DMSO (6 ml) and benzene (3 ml), and thereto were added pyridine (0.18 ml) and trifluoroacetic acid (0.09 ml). After ice-cooling the mixture, DCC (941 mg) was added thereto, and the mixture was stirred at room temperature for 2.5 hours. The precipitated dicyclohexylurea was filtered off, and the filtrate was poured into ice-cold 1N hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine successively, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluate: chloroform-methanol) to give 759 mg of the title compound.

Workup

  1. additionwas added
  2. filtrationThe precipitated dicyclohexylurea was filtered off
  3. additionthe filtrate was poured into ice-cold 1N hydrochloric acid
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (eluate: chloroform-methanol)

Sources & evidence

ORD record
ord-ab0abd58a2c848b9ace7dbc3dd2f791e
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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