Hydrochloric Acid → HCID 67296202, compound

HRID 2276839Notes

Reaction equation

HRID 2276839 reaction equation
C([O:3][C:4](=[O:33])[C:5]([CH3:32])([O:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[CH2:18][CH2:17][C@H:16]([NH:19][C@@H:20]([C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24][CH:23]=3)[CH3:21])[CH2:15]2)=[CH:10][CH:9]=1)[CH3:6])C.[OH-].[K+].[ClH:36]>C(O)C.O1CCCC1.C(OCC)(=O)C>[ClH:36].[CH3:6][C:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[CH2:18][CH2:17][C@H:16]([NH:19][C@@H:20]([C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24][CH:23]=3)[CH3:21])[CH2:15]2)=[CH:10][CH:9]=1)([CH3:32])[C:4]([OH:33])=[O:3]

Participants

7

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14797Potassium HydroxideHCID 67296455HCID 67296455, compound

Product 1

HCID 67296202HCID 67296202, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

2-Methyl-2-{4-[(1R,3S)-3-{[(1R)-1-(naphthalen-1-yl)ethyl]amino}cyclopentyl]phenoxy}propanoic acid ethyl ester (130 mg, 0.29 mmol) was dissolved in ethanol (2 mL) and tetrahydrofuran (2 mL), followed by addition of 2N aqueous potassium hydroxide solution, and the mixture was stirred overnight 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 ethyl acetate, 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 ethyl acetate (3 mL), followed by addition of an ethyl acetate solution of 1N hydrochloric acid (1 mL), and 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 (102 mg, 77%).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. extractionThe aqueous phase was extracted with ethyl acetate
  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-e56ebb62c36544beb5b0b14c62aa401c
Source dataset
uspto-grants-2015_09
Patent number
US09133140B2

Reaction notes

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