Ammonia → 3-(4-{1-((Tert-butoxycarbonyl-heptyl-amino)-methyl]-cyclopropyl}-phenyl)-2-ethoxy-propionic acid methyl ester

HRID 47807Notes

Reaction equation

HRID 47807 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[C:5]([O:32][CH2:33][CH3:34])=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2([CH2:16][N:17]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)C.[Mg].N>CO.BrCCBr>[CH3:1][O:3][C:4](=[O:35])[CH:5]([O:32][CH2:33][CH3:34])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2([CH2:16][N:17]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:14][CH2:15]2)=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 5462224Magnesium5×HCID 69884403HCID 69884403, compound

Product 1

HCID 698840843-(4-{1-((Tert-butoxycarbonyl-heptyl-amino)-methyl]-cyclopropyl}-phenyl)-2-ethoxy-propionic acid methyl esterYield 87.1%

Reagents, catalysts & solvents 2

HCID 78391,2-DibromoethaneCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(4-{1-[(tert-butoxycarbonyl-heptyl-amino)-methyl]-cyclopropyl}-phenyl)-2-ethoxy-acrylic acid ethyl ester (680 mg, 1.40 mmol) in anhydrous methanol (20 mL) in a flame dried round bottom flask under an nitrogen atmosphere was added magnesium turnings (53.50 mmol, 85 mg). After 30 min, 1,2-dibromoethane (1 drop) was added directly to the magnesium turnings via pipette, initiating H2 gas evolution from the magnesium. At this time a dry stir bar was added and the mixture was stirred at room temperature until all of the magnesium solid had dissolved. Two additional portions of magnesium (80 mg) were added and allowed to dissolve (16 h). The mixture was poured over 25 mL of ice cooled 2NHCl. The acidic mixture was brought to pH 8.5 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-{1-[(tert-butoxycarbonyl-heptyl-amino)-methyl]-cyclopropyl}-phenyl)-2-ethoxy-propionic acid methyl ester as a clear oil (580 mg, 87%).

Workup

  1. additionwas added
  2. dissolutionhad dissolved
  3. dissolutionto dissolve (16 h)
  4. extractionwas extracted with diethyl ether (3×)
  5. washwashed with saturated NaCl (3×)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-73df859b7f1943e3b36205d53aa917e5
Source dataset
uspto-grants-2004_03
Patent number
US06699904B2

Reaction notes

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