7-[(R)-2-((E)-3-Hydroxy-4-phenyl-but-1-enyl)-6-oxo-piperidin-1-yl]-heptanoic acid → 7-[(R)-2-((E)-3-Hydroxy-4-phenyl-but-1-enyl)-6-oxo-piperidin-1-yl]-heptanoic acid isopropyl ester

HRID 2052931Notes

Reaction equation

HRID 2052931 reaction equation
[OH:1][CH:2]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)/[CH:3]=[CH:4]/[C@H:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[N:6]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19].[CH:28](N=NNC1C=CC(C)=CC=1)([CH3:30])[CH3:29]>CC(C)=O>[CH:28]([O:19][C:18](=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N:6]1[C:7](=[O:11])[CH2:8][CH2:9][CH2:10][C@@H:5]1/[CH:4]=[CH:3]/[CH:2]([OH:1])[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([CH3:30])[CH3:29]

Participants

4

Reactant 2

HCID 116892927-[(R)-2-((E)-3-Hydroxy-4-phenyl-but-1-enyl)-6-oxo-piperidin-1-yl]-heptanoic acidHCID 130172131-Isopropyl-3-p-tolyltriazene

Product 1

HCID 113390017-[(R)-2-((E)-3-Hydroxy-4-phenyl-but-1-enyl)-6-oxo-piperidin-1-yl]-heptanoic acid isopropyl esterYield 47.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 7-[(R)-2-((E)-3-hydroxy-4-phenyl-but-1-enyl)-6-oxo-piperidin-1-yl]-heptanoic acid (9.7 mg, 0.026 mmol), 1-isopropyl-3-p-tolyltriazene (5 mg, 0.028 mmol) and acetone (0.5 mL) was stirred at rt for 18 h. The reaction was quenched with saturated aqueous NH4Cl (2 mL) and extracted with CH2Cl2 (3×3 mL). The combined organic phase was dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (50% CH2Cl2/Hexane→CH2Cl2→2% MeOH/CH2Cl2, gradient) afforded 5.1 mg (47%) of the title compound.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl (2 mL)
  2. extractionextracted with CH2Cl2 (3×3 mL)
  3. dry with materialThe combined organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash column chromatography on silica gel (50% CH2Cl2/Hexane→CH2Cl2→2% MeOH/CH2Cl2, gradient)

Sources & evidence

ORD record
ord-c89fbc9307114fd1ad8be0a3a8143b89
Source dataset
uspto-grants-2008_02
Patent number
US07326716B2

Reaction notes

Loading…