Hydrochloric Acid → HCID 67296065, compound

HRID 2276848Notes

Reaction equation

HRID 2276848 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]2[CH2:17][CH2:16][C@H:15]([NH:18][C@@H:19]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:24]([F:31])=[CH:23][CH:22]=3)[CH3:20])[CH2:14]2)=[CH:9][CH:8]=1)C.[OH-].[Na+].Cl>C(O)C>[F:31][C:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21]([C@H:19]([NH:18][C@H:15]2[CH2:16][CH2:17][C@@H:13]([C:10]3[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:32])=[O:3])=[CH:8][CH:9]=3)[CH2:14]2)[CH3:20])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67296163HCID 67296163, compound

Product 1

HCID 67296065HCID 67296065, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

{4-[(1R,3S)-3-{[(1R)-1-(4-Fluoronaphthalen-1-yl)ethyl]amino}cyclopentyl]phenoxy}acetic acid ethyl ester (800 mg, 1.8 mmol) was dissolved in ethanol (5 mL), followed by addition of 1N aqueous sodium hydroxide solution (5 mL), and the mixture was stirred for 30 minutes at room temperature. 1N hydrochloric acid was added dropwise to the reaction mixture to make the reaction solution acidic, and the solvent was distilled off under reduced pressure. The aqueous phase was extracted with chloroform, the extracted solution was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to give the title compound (742 mg, 99%).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. extractionThe aqueous phase was extracted with chloroform
  3. dry with materialthe extracted solution was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0f94b7e7955b479ea0388dfdd9c1a3d9
Source dataset
uspto-grants-2015_09
Patent number
US09133140B2

Reaction notes

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