HCID 86753666, compound → HCID 15380364, compound

HRID 361744Notes

Reaction equation

HRID 361744 reaction equation
C([O:8][C:9](=[O:35])[CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:34])[C:18]([CH3:33])([CH3:32])[CH2:19][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>[OH-].[Pd+2].[OH-].O.CO>[C:28]([C:25]1[CH:24]=[CH:23][C:22]([C:21]([NH:20][CH2:19][C:18]([CH3:33])([CH3:32])[C:17]([N:14]2[CH2:13][CH2:12][CH:11]([CH2:10][C:9]([OH:35])=[O:8])[CH2:16][CH2:15]2)=[O:34])=[O:31])=[CH:27][CH:26]=1)(=[NH:29])[NH2:30]

Participants

4

Reactant 1

HCID 86753666HCID 86753666, compound

Product 1

HCID 15380364HCID 15380364, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

N-(N-4-Amidinobenzoyl-α,α-dimethyl-β-alanyl)-4-piperidineacetic acid benzyl ester (0.10 g) was stirred under a hydrogen atmosphere in a 50% water/methanol mixed solution under the presence of palladium hydroxide catalyst at a room temperature for 6 hours. The catalyst was removed by filtration and the solvents were distilled off. The residue was dissolved in a 1N aqueous solution of acetic acid and the resulting solution was purified with a high performance liquid chromatography (HPLC) [column: ODS 5C18 (μ bondasphere, φ 19×150 mm), mobile phase: (A) 0.1% TFA, (B) 100% CH3CN/0.1% TFA, gradient: (A):(B)=80:20-70:30, 20 minutes, flow rate: 17 ml/min]. The desired fractions were collected and lyophilized to yield N-(N-4-amidinobenzoyl-α,α-dimethyl-β-alanyl)-4-piperidineacetic acid (15 ml).

Workup

  1. customThe catalyst was removed by filtration
  2. distillationthe solvents were distilled off
  3. dissolutionThe residue was dissolved in a 1N aqueous solution of acetic acid
  4. customthe resulting solution was purified with a high performance liquid chromatography (HPLC) [column: ODS 5C18 (μ bondasphere, φ 19×150 mm), mobile phase: (A) 0.1% TFA, (B) 100% CH3CN/0.1% TFA, gradient: (A):(B)=80:20-70:30, 20 minutes, flow rate: 17 ml/min]
  5. customThe desired fractions were collected

Sources & evidence

ORD record
ord-6224e6d17172489d84ea96c4fe8434a0
Source dataset
uspto-grants-1999_02
Patent number
US05866592

Reaction notes

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