Magnesium → HCID 69883929, compound

HRID 47792Notes

Reaction equation

HRID 47792 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[C:5]([O:30][CH2:31][CH3:32])=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][N:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:9][CH:8]=1)C.[Mg]>CO>[CH3:1][O:3][C:4](=[O:33])[CH:5]([O:30][CH2:31][CH3:32])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][N:15]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 5462224Magnesium2×HCID 698846713-{4-[2-(Tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-ethoxy-acrylic acid ethyl ester

Product 1

HCID 69883929HCID 69883929, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-ethoxy-acrylic acid ethyl ester (1.11 mmol, 510 mg) dissolved in anhydrous methanol (20 mL) was added dry magnesium turnings (2.77 mmol, 67 mg). The resulting solution was allowed to stir at room temperature, with additional portions of magnesium being added after dissolution of the previous portion until the starting material had been consumed as determined by mass spectrometry. The mixture was poured over 25 mL of ice cooled 2M HCl. The acidic mixture was brought to pH 9 by the addition of concentrated aqueous ammonia, then was extracted with diethyl ether (3×). The organic layers were combined, washed with saturated NaCl (3×), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-ethoxy-propionic acid methyl ester as a clear oil (437 mg, 88%).

Workup

  1. additionadded
  2. dissolutionafter dissolution of the previous portion until the starting material
  3. customhad been consumed
  4. additionThe mixture was poured over 25 mL of ice
  5. temperaturecooled 2M HCl
  6. additionThe acidic mixture was brought to pH 9 by the addition of concentrated aqueous ammonia
  7. extractionwas extracted with diethyl ether (3×)
  8. washwashed with saturated NaCl (3×)
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-978afcc273cd48f9ba118283aa5a9e08
Source dataset
uspto-grants-2004_03
Patent number
US06699904B2

Reaction notes

Loading…