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 349328Notes

Reaction equation

HRID 349328 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-1729f7191b704020ba35ca233e97aa1a
Source dataset
uspto-grants-2007_02
Patent number
US07179820B2

Reaction notes

Loading…