Hydrochloric Acid → HCID 22591751, compound

HRID 22893Notes

Reaction equation

HRID 22893 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH:8]=2)[CH2:5][CH:4]([C:22]([NH:24][CH:25]([C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[CH2:26][C:27]([O:29]CC)=[O:28])=[O:23])[CH2:3]1.[OH-].[Na+].Cl>>[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH:8]=2)[CH2:5][CH:4]([C:22]([NH:24][CH:25]([C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[CH2:26][C:27]([OH:29])=[O:28])=[O:23])[CH2:3]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22591842HCID 22591842, compound

Product 1

HCID 22591751HCID 22591751, compound

Procedure

To a solution of ethyl 3-({5-oxo-1-(3-(piperidylcarbonylamino)phenyl)pyrrolidin-3-yl}carbonylamino)-3-(3-pyridyl)propanoate (169 mg, 0.333 mmol, 1.0 eq) was added a solution of NaOH (0.84 mL, 2.0 M, 1.67 mmol, 5.0 eq). After the reaction mixture was stirred at room temperature overnight, it was neutralized with a solution of aqueous HCl (0.84 mL, 2.0 M, 1.67 mmol). Following removal of solvent under reduced pressure, product was dissolved in 10% MeOH-CH2Cl2, and filtered. Concentration under reduced pressure afforded the title compound as an orange solid. 1H NMR (DMSO-d6, 400 MHz): δ 1.47 (m, 4), 1.56 (m, 2), 2.56-2.77 (m, 2), 2.82 (m, 2), 3.29 (m, 5), 3.73-3.83 (m, 1), 3.91-4.01 (m, 1), 5.25 (m, 1), 7.19 (m, 1), 7.28 (m, 1), 7.55 (m, 1), 7.70 (d, 1 J =12.5), 7.96 (d, 1, J =7.9), 8.50 (d, 1, J=8.7), 8.55 (m, 1), 8.65 (s, 1), 8.82 (d, 1, J=7.8), 12.4 (br s, 1). MS (ES+): 480 (M+H)+; (ES−) 478 (M−H)−.

Workup

  1. customremoval of solvent under reduced pressure, product
  2. dissolutionwas dissolved in 10% MeOH-CH2Cl2
  3. filtrationfiltered
  4. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-76d52014f6ae49d9882c147c2659ae52
Source dataset
uspto-grants-2005_02
Patent number
US06849639B2

Reaction notes

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