Water → HCID 71610756, compound

HRID 714036Notes

Reaction equation

HRID 714036 reaction equation
[OH-].[Na+:2].[CH2:3]([C:5]1[CH:34]=[C:33]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)[C:32]([OH:42])=[CH:31][C:6]=1[O:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[C:13]([CH2:28][CH2:29][CH3:30])=[C:14]([NH:18][C:19](=[O:27])[CH2:20][C:21]([CH3:26])([CH3:25])[C:22]([OH:24])=[O:23])[CH:15]=[CH:16][CH:17]=1)[CH3:4].O>C1COCC1>[CH2:3]([C:5]1[CH:34]=[C:33]([C:35]2[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=2)[C:32]([OH:42])=[CH:31][C:6]=1[O:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[C:13]([CH2:28][CH2:29][CH3:30])=[C:14]([NH:18][C:19](=[O:27])[CH2:20][C:21]([CH3:26])([CH3:25])[C:22]([O-:24])=[O:23])[CH:15]=[CH:16][CH:17]=1)[CH3:4].[Na+:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 71610757HCID 71610757, compound

Product 1

HCID 71610756HCID 71610756, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 1 N sodium hydroxide (404 mL) dropwise to a solution of 4-[[3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxy-phenoxy]propoxy]-2-propyl-phenyl]amino]-2,2-dimethyl-4-oxo-butanoic acid (223 g, 404 mmol) in THF (1115 mL) and stir at ambient temperature for 15 min. Reduce the volume in vacuo and add water (1300 mL). Remove additional solvent using a membrane pump, to avoid heating the solution, to obtain a final volume of 1250 mL. Lyophilize the remaining solution in batches to yield the title compound (230 g, 99%) as an off-white solid. ES/MS m/z 552 (M+1, free base).

Workup

  1. customRemove additional solvent
  2. temperatureto avoid heating the solution
  3. customto obtain a final volume of 1250 mL

Sources & evidence

ORD record
ord-12edcf2438ea44a896664a2e8cdcec58
Source dataset
uspto-grants-2015_11
Patent number
US09187411B2

Reaction notes

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