Hydrochloric Acid → HCID 9803820, compound

HRID 1862531Notes

Reaction equation

HRID 1862531 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]([N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24]([NH:26][CH2:27][C@H:28]([NH:32][C:33](=[O:35])[CH3:34])[C:29]([OH:31])=[O:30])=[O:25])[CH2:19]2)=[O:17])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[NH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]([N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24]([NH:26][CH2:27][C@H:28]([NH:32][C:33](=[O:35])[CH3:34])[C:29]([OH:31])=[O:30])=[O:25])[CH2:19]2)=[O:17])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12991326HCID 12991326, compound

Product 1

HCID 9803820HCID 9803820, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl]-3-piperidylcarbonyl]-2(S)-acetylamino-β-alanine (14.9 g) in ethyl acetate (150 ml) was added dropwise 4N HCl in ethyl acetate (74.8 ml) for 10 minutes at 0° C. After the mixture was stirred for 1 hour and 20 minutes, a white solid was collected by filtration, and dried in vacuo. The powder was dissolved in water (150 ml), and the solution was neutralized to pH 6.5 with saturated aqueous NaHCO3. The solution was concentrated to about 100 ml, then applied to ODS column (Disogel-120SP®, 1 l), and eluted with 4-6% CH3CN/water. The eluent was concentrated in vacuo, and the residue was dissolved 0.5% aqueous ethanol (200 ml). After the mixture was stirred at room temperature overnight, the resultant solid was collected by filtration, and dried in vacuo to give N-[(R)-1-[3-(4-piperidyl)propionyl]-3-piperidylcarbonyl]-2-(S)-acetylamino-β-alanine (6.85 g) as a white crystal.

Workup

  1. filtrationa white solid was collected by filtration
  2. customdried in vacuo
  3. dissolutionThe powder was dissolved in water (150 ml)
  4. concentrationThe solution was concentrated to about 100 ml
  5. washeluted with 4-6% CH3CN/water
  6. concentrationThe eluent was concentrated in vacuo
  7. dissolutionthe residue was dissolved 0.5% aqueous ethanol (200 ml)
  8. stirringAfter the mixture was stirred at room temperature overnight
  9. filtrationthe resultant solid was collected by filtration
  10. customdried in vacuo

Sources & evidence

ORD record
ord-745b714df9cf48878c50d0ec26401206
Source dataset
uspto-grants-2003_03
Patent number
US06538007B1

Reaction notes

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