Hydrochloric Acid → HCID 67296041, compound

HRID 2276832Notes

Reaction equation

HRID 2276832 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][NH:6][C:7](=[O:32])[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)C.[OH-].[Na+].[ClH:36]>C(O)C>[ClH:36].[C:22]1([C@H:20]([NH:19][C@H:16]2[CH2:17][CH2:18][C@@H:14]([C:11]3[CH:10]=[CH:9][C:8]([C:7]([NH:6][CH2:5][C:4]([OH:33])=[O:3])=[O:32])=[CH:13][CH:12]=3)[CH2:15]2)[CH3:21])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67296075HCID 67296075, compound

Product 1

HCID 67296041HCID 67296041, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-{4-[(1R,3S)-3-{[(1R)-1-(Naphthalen-1-yl)ethyl]amino}cyclopentyl]benzoyl}glycine ethyl ester (139 mg, 0.31 mmol) was dissolved in ethanol (2 mL), followed by addition of 1N aqueous sodium hydroxide (2 mL), and the mixture was stirred for 4 hours 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. Diisopropyl ether and water were added to the reaction mixture, followed by ultrasonic wave treatment, and then the solid generated was collected by filtration to give the title compound (52 mg, 37%).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionDiisopropyl ether and water were added to the reaction mixture
  3. filtrationthe solid generated was collected by filtration

Sources & evidence

ORD record
ord-6be81739313040a0b02ec8d5764880cf
Source dataset
uspto-grants-2015_09
Patent number
US09133140B2

Reaction notes

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