Hydrochloric Acid → HCID 67296472, compound

HRID 2276847Notes

Reaction equation

HRID 2276847 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C@H:12]([NH:14][CH:15]2[CH2:19][CH2:18][C@@H:17]([C:20]3[CH:31]=[CH:30][C:23]([O:24][CH2:25][C:26]([O:28]C)=[O:27])=[CH:22][CH:21]=3)[CH2:16]2)[CH3:13])=[CH:4][CH:3]=1.[OH-].[K+].Cl>CO.O>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C@H:12]([NH:14][CH:15]2[CH2:19][CH2:18][C@@H:17]([C:20]3[CH:31]=[CH:30][C:23]([O:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:22][CH:21]=3)[CH2:16]2)[CH3:13])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 67296522HCID 67296522, compound

Product 1

HCID 67296472HCID 67296472, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl {4-[(1R)-3-{[(1R)-1-(4-fluoronaphthalen-1-yl)ethyl]amino}cyclopentyl]phenoxy}acetate (72 mg, 0.17 mmol) and potassium hydroxide (56 mg, 1.0 mmol) in methanol (2 mL) and water (0.5 mL) was heated under reflux for 2 hours. 2N hydrochloric acid was added to the reaction solution to make the pH 7, and the solution was purified by high performance liquid chromatography (water:acetonitrile) to give the title compound (a mixture of diastereomers) (36 mg, 52%).

Workup

  1. temperatureunder reflux for 2 hours
  2. customthe solution was purified by high performance liquid chromatography (water:acetonitrile)

Sources & evidence

ORD record
ord-e9cc24867d134604a73235aec96a562a
Source dataset
uspto-grants-2015_09
Patent number
US09133140B2

Reaction notes

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