Acetic Acid → N-4-amidinobenzoyl-beta-phenyl-alpha,alpha-dimethyl-beta-alanyl-4-piperidineacetic acid

HRID 361750Notes

Reaction equation

HRID 361750 reaction equation
C([O:8][C:9](=[O:41])[CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:40])[C:18]([CH3:39])([CH3:38])[CH:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[NH:20][C:21](=[O:31])[C:22]2[CH:27]=[CH:26][C:25]([C:28](=[NH:30])[NH2:29])=[CH:24][CH:23]=2)[CH2:13][CH2:12]1)C1C=CC=CC=1.C(O)(=O)C.[H][H]>CO.[OH-].[Pd+2].[OH-]>[C:28]([C:25]1[CH:24]=[CH:23][C:22]([C:21]([NH:20][CH:19]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:18]([CH3:39])([CH3:38])[C:17]([N:14]2[CH2:13][CH2:12][CH:11]([CH2:10][C:9]([OH:41])=[O:8])[CH2:16][CH2:15]2)=[O:40])=[O:31])=[CH:27][CH:26]=1)(=[NH:29])[NH2:30]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 86753669N-4-amidinobenzoyl-beta-phenyl-alpha,alpha-dimethyl-beta-alanyl-4-piperidineacetic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 9825696N-4-amidinobenzoyl-beta-phenyl-alpha,alpha-dimethyl-beta-alanyl-4-piperidineacetic acidYield 89.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

N-4-Amidinobenzoyl-β-phenyl-α,α-dimethyl-β-alanyl-4-piperidineacetic acid benzyl ester (63 mg, 0.114 mmol) was dissolved in an 80% aqueous methanol solution (10 ml) containing 2% acetic acid. To the reulting solution was added palladium hydroxide (50 mg) and the mixture was stirred in a hydrogen atmosphere for 15 minutes. The solvents were distilled off and the res idue was dissolved in a 1N aqueous solution of acetic acid. The resulting solution was purified with a high performance liquid chromatography (HPLC) under the same conditions as described in (3) to yield a powder of N-(N-4-amidinobenzoyl-β-phenyl-α,α-dimethyl-β-alanyl-4-piperidineacetic acid (47.5 mg, 89.9%). The obtained product was identified by NMR, MS and HPLC analyses to be the same compound as prepared by the solid phase method.

Workup

  1. distillationThe solvents were distilled off
  2. dissolutionthe res idue was dissolved in a 1N aqueous solution of acetic acid
  3. customThe resulting solution was purified with a high performance liquid chromatography (HPLC) under the same conditions

Sources & evidence

ORD record
ord-a3f40aaa88104692bf62d25fccc98543
Source dataset
uspto-grants-1999_02
Patent number
US05866592

Reaction notes

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