Water → HCID 86611401, compound

HRID 1184796Notes

Reaction equation

HRID 1184796 reaction equation
[CH2:1]([O:3][CH:4]([CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1)[CH2:5][S:6][C:7]1[CH:17]=[CH:16][C:10]([O:11][CH2:12][C:13]([OH:15])=[O:14])=[C:9]([CH3:18])[CH:8]=1)[CH3:2].[NH2:31][C@H:32]([C:38]([OH:40])=[O:39])[CH2:33][CH2:34][CH2:35][CH2:36][NH2:37].O>CO>[OH2:3].[OH2:39].[NH2:31][C@H:32]([C:38]([OH:40])=[O:39])[CH2:33][CH2:34][CH2:35][CH2:36][NH2:37].[CH2:1]([O:3][CH:4]([CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:29])([F:28])[F:30])=[CH:23][CH:22]=1)[CH2:5][S:6][C:7]1[CH:17]=[CH:16][C:10]([O:11][CH2:12][C:13]([OH:15])=[O:14])=[C:9]([CH3:18])[CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 5962L-LysineHCID 11476297HCID 11476297, compound

Product 1

HCID 86611401HCID 86611401, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4 L Erlenmeyer flask equipped with a magnetic stir bar and nitrogen outlet was charged with {4-[2-ethoxy-3-(4-trifluoromethyl-phenoxy)-propylsulfanyl]-2-methyl-phenoxy}-acetic acid (502 g, 1.05 mol 93% purity) and methanol (2.3 L). The flask was warmed on a hot plate with stirring and then charged with L-Lysine (153.5 g, 1.05 mmol). The reaction mixture was diluted with water (112.5 mL, 6.25 mol). The reaction mixture was stirred and heated until the solids were dissolved. Upon reaching reflux the light yellow solution was hot filtered through a pad of Celite and the resulting light yellow solution was allowed to slowly cool to room temperature and then held at room temperature, with stirring for 3 days. The solid was isolated by vacuum filtration, the filter pad was rinsed with 1% (v/v) H2O in methanol (˜400 mL). The resulting solid was slurried in methanol (1 L) then filtered to yield the title compound as a white solid (lysine salt; di-hydrate).

Workup

  1. customA 4 L Erlenmeyer flask equipped with a magnetic stir bar and nitrogen outlet
  2. temperatureThe flask was warmed on a hot plate
  3. stirringThe reaction mixture was stirred
  4. temperatureheated until the solids
  5. dissolutionwere dissolved
  6. temperatureUpon reaching reflux the light yellow solution
  7. filtrationwas hot filtered through a pad of Celite
  8. customheld at room temperature
  9. stirringwith stirring for 3 days
  10. customThe solid was isolated by vacuum filtration
  11. washthe filter pad was rinsed with 1% (v/v) H2O in methanol (˜400 mL)
  12. filtrationthen filtered

Sources & evidence

ORD record
ord-9369e4f463ca41daba2daf58c7de7075
Source dataset
uspto-grants-2014_03
Patent number
US08669288B2

Reaction notes

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