Hydrochloric Acid → HCID 67296019, compound

HRID 2276833Notes

Reaction equation

HRID 2276833 reaction equation
C(OC([N:8]([C@@H:24]([C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1)[CH3:25])[C@H:9]1[CH2:13][CH2:12][C@@H:11]([C:14]2[CH:15]=[C:16]([CH2:20][C:21]([OH:23])=[O:22])[CH:17]=[CH:18][CH:19]=2)[CH2:10]1)=O)(C)(C)C.[ClH:36]>O1CCOCC1>[ClH:36].[C:26]1([C@H:24]([NH:8][C@H:9]2[CH2:13][CH2:12][C@@H:11]([C:14]3[CH:15]=[C:16]([CH2:20][C:21]([OH:23])=[O:22])[CH:17]=[CH:18][CH:19]=3)[CH2:10]2)[CH3:25])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67296435HCID 67296435, compound

Product 1

HCID 67296019HCID 67296019, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

{3-[(1R,3S)-3-{(tert-Butoxycarbonyl)[(1R)-1-(naphthalen-1-yl)ethyl]amino}cyclopentyl]phenyl}acetic acid (417 mg, 0.88 mmol) was dissolved in 1,4-dioxane (6 mL), followed by addition of a 1,4-dioxane solution of 4N hydrochloric acid (2 mL), and the mixture was stirred for 2 days at room temperature. The reaction solvent was distilled off under reduced pressure, followed by addition of water and methylene chloride. Then, the mixture was neutralized with a 1N aqueous sodium hydroxide solution, and was then extracted with methylene chloride. After the extracted solution was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained residue 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. Hexane was added to the residue, followed by ultrasonic wave treatment, and then the solid matter generated was collected by filtration to give the title compound (324 mg, 90%).

Workup

  1. distillationThe reaction solvent was distilled off under reduced pressure
  2. additionfollowed by addition of water and methylene chloride
  3. extractionwas then extracted with methylene chloride
  4. dry with materialAfter the extracted solution was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. dissolutionThe obtained residue was dissolved in methylene chloride (6 mL)
  7. additionfollowed by addition of an ethyl acetate solution of 1N hydrochloric acid (2 mL)
  8. distillationthe solvent was distilled off under reduced pressure
  9. additionHexane was added to the residue
  10. filtrationthe solid matter generated was collected by filtration

Sources & evidence

ORD record
ord-e41744eee89e41658f36907c406e6d64
Source dataset
uspto-grants-2015_09
Patent number
US09133140B2

Reaction notes

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