Hydrochloric Acid → HCID 67296283, compound

HRID 2276838Notes

Reaction equation

HRID 2276838 reaction equation
C([O:3][C:4](=[O:31])[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)[CH:24]=[CH:23][CH:22]=3)[CH3:20])[CH2:14]2)=[CH:9][CH:8]=1)C.[OH-].[Na+].[ClH:34].C(OCC)(=O)C>C(O)C.C(Cl)Cl>[ClH:34].[C:21]1([C@H:19]([NH:18][C@H:15]2[CH2:16][CH2:17][C@@H:13]([C:10]3[CH:9]=[CH:8][C:7]([O:6][CH2:5][C:4]([OH:31])=[O:3])=[CH:12][CH:11]=3)[CH2:14]2)[CH3:20])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 59617257HCID 59617257, compound

Product 1

HCID 67296283HCID 67296283, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

{4-[(1R,3S)-3-{[(1R)-1-(Naphthalen-1-yl)ethyl]amino}cyclopentyl]phenoxy}acetic acid ethyl ester (720 mg, 1.7 mmol) was dissolved in ethanol (5 mL), followed by addition of 1N aqueous sodium hydroxide solution (5 mL), and the mixture was stirred for 1 hour at room temperature. 1N hydrochloric acid was added dropwise to the reaction mixture to make the reaction solution acidic, and then the solvent was distilled off under reduced pressure. The aqueous phase was extracted with methylene chloride, the extracted solution was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue obtained was dissolved in methylene chloride (6 mL), followed by addition of an ethyl acetate solution of 1N hydrochloric acid (2 mL), and then the solvent was distilled off under reduced pressure. Ethyl acetate and hexane were added to the residue, followed by treatment with ultrasonic waves, and then the solid matter generated was collected by filtration to give the title compound (237 mg, 87%).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. extractionThe aqueous phase was extracted with methylene chloride
  3. dry with materialthe extracted solution was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue obtained
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionEthyl acetate and hexane were added to the residue
  8. filtrationthe solid matter generated was collected by filtration

Sources & evidence

ORD record
ord-c851123870024aefacf8db5422e3b892
Source dataset
uspto-grants-2015_09
Patent number
US09133140B2

Reaction notes

Loading…