HCID 22717915, compound → HCID 9911854, compound

HRID 1368892Notes

Reaction equation

HRID 1368892 reaction equation
C(OC([NH:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][C:17]([O:30][P:31]([CH:34]([NH:38][C:39](=[O:48])[CH2:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:35]([CH3:37])[CH3:36])([OH:33])=[O:32])([C:20]([O:22]CC2C=CC=CC=2)=[O:21])[CH2:16][CH2:15]1)=O)C1C=CC=CC=1>O1CCOCC1.O.[OH-].[Pd+2].[OH-]>[NH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][C:17]([O:30][P:31]([CH:34]([NH:38][C:39](=[O:48])[CH2:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:35]([CH3:36])[CH3:37])([OH:33])=[O:32])([C:20]([OH:22])=[O:21])[CH2:16][CH2:15]1

Participants

5

Reactant 1

HCID 22717915HCID 22717915, compound

Product 1

HCID 9911854HCID 9911854, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

The benzyl 1-(2-benzyloxycarbonylaminoethyl)-4-((2-methyl-1-(3-phenylpropanoylamino)propyl)(hydroxyphosphinoyl)oxy)piperidine-4-carboxylate (56 mg) obtained in the above step (f) was dissolved in a mixed solvent of dioxane (1.5 ml) and water (0.5 ml), and then the solution was added with palladium hydroxide (13 mg). The mixture was stirred under a hydrogen atmosphere at room temperature for 3 hours. The reaction mixture was filtered with celite, and then the solvent was evaporated. The residue was purified with HP-20 (Diaion, 40 cc, methanol:water=1:1 to acetone:water=1:4)) to obtain the title compound:1-(2-aminoethyl)-4-((2-methyl-1-(3-phenylpropionylamino)propyl)(hydroxyphosphinoyl)oxy)piperidine-4-carboxylic acid (32 mg, 84%).

Workup

  1. filtrationThe reaction mixture was filtered with celite
  2. customthe solvent was evaporated
  3. customThe residue was purified with HP-20 (Diaion, 40 cc, methanol:water=1:1 to acetone:water=1:4))

Sources & evidence

ORD record
ord-8da8eff165214496bba8b53a08fd21e5
Source dataset
uspto-grants-2003_06
Patent number
US06576627B1

Reaction notes

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