D-Tartaric acid → HCID 131726320, compound

HRID 1269497Notes

Reaction equation

HRID 1269497 reaction equation
[C:1]([OH:10])(=[O:9])[C@H:2]([C@@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].[CH2:11]([O:18][C:19](=[O:36])[C:20]([CH3:35])([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]2[CH2:34][CH2:33][CH2:32][NH:31][CH2:30]2)[CH:24]=1)[CH3:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CC(=O)CC>[C:6]([C@H:4]([C@@H:2]([C:1]([OH:10])=[O:9])[OH:3])[OH:5])([OH:8])=[O:7].[CH2:11]([O:18][C:19](=[O:36])[C:20]([CH3:21])([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C@H:29]2[CH2:34][CH2:33][CH2:32][NH:31][CH2:30]2)[CH:24]=1)[CH3:35])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 439655D-Tartaric acid2×HCID 688839562-Methyl-2-(3-piperidin-3-yl-phenoxy)-propionic acid benzyl ester

Product 1

HCID 131726320HCID 131726320, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

D-(−)-tartaric acid (3.80 g, 25.3 mmol) was suspended in 105 mL of 2-butanone containing 2.5% water, then the suspension was warmed to reflux to give a clear solution. (R)-enriched 2-methyl-2-(3-piperidin-3-yl-phenoxy)-propionic acid benzyl ester (9.10 g, 25.7 mmol) was dissolved in 15 mL of of 2-butanone containing 2.5% water and was then added to the refluxing solution of D-(−)-tartaric acid. The reaction solution stirred at reflux for 15 minutes, then cooled slowly to room temperature and stirred for 16 hr. The resulting white precipitate was collected by filtration and rinsed with 2-butanone followed by drying in vacuo to give (R)-2-methyl-2-(3-piperidin-3-yl-phenoxy)-propionic acid benzyl ester-(D)-tartrate salt (9.64 g, 89%, 93% e.e.) as a white solid.

Workup

  1. temperaturethe suspension was warmed
  2. temperatureto reflux
  3. customto give a clear solution
  4. temperatureat reflux for 15 minutes
  5. stirringstirred for 16 hr
  6. filtrationThe resulting white precipitate was collected by filtration
  7. washrinsed with 2-butanone
  8. customby drying in vacuo

Sources & evidence

ORD record
ord-64f96e445e34422d88c9adc78c67dc35
Source dataset
uspto-grants-2007_04
Patent number
US07199243B2

Reaction notes

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