Pyridine → HCID 22860068, compound

HRID 1720510Notes

Reaction equation

HRID 1720510 reaction equation
C([O:8][C:9]1[CH:40]=[CH:39][C:12]([O:13][CH2:14][CH:15]([CH:17]2[CH2:21][CH2:20][CH2:19][N:18]2[C:22](=[O:38])[C@@H:23]2[CH2:27][CH2:26][CH2:25][N:24]2[C:28](=[O:37])[CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[OH:16])=[CH:11][CH:10]=1)C1C=CC=CC=1.N1C=CC=CC=1.FC(F)(F)C(O)=O.C1CCC(N=C=NC2CCCCC2)CC1>CS(C)=O>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][C:15]([C@@H:17]2[CH2:21][CH2:20][CH2:19][N:18]2[C:22](=[O:38])[C@@H:23]2[CH2:27][CH2:26][CH2:25][N:24]2[C:28](=[O:37])[CH2:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:16])=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 54142722HCID 54142722, compound

Product 1

HCID 22860068HCID 22860068, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (2S)-2-{2-(2-[4-(benzyloxy)phenoxy]-1-hydroxyethyl}-1-[N-(3-phenylpropionyl)-L-prolyl]pyrrolidine (1.81 g) in DMSO (30 ml) were added pyridine (0.3 ml), trifluoroacetic acid (0.15 ml) and DCC (1.2 g), and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The extract 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 1.45 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract 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-7250d582d13242909483b414a79fab69
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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