HCID 15517691, compound → HCID 9801884, compound

HRID 1368873Notes

Reaction equation

HRID 1368873 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([O:27][P:28]([CH:31]([NH:35][C:36](=[O:45])[CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH:32]([CH3:34])[CH3:33])([OH:30])=[O:29])[C:17]([O:19]CC1C=CC=CC=1)=[O:18])=O)C1C=CC=CC=1>O1CCOCC1.O.[OH-].[Pd+2].[OH-]>[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([O:27][P:28]([CH:31]([NH:35][C:36](=[O:45])[CH2:37][CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[CH:32]([CH3:34])[CH3:33])([OH:30])=[O:29])[C:17]([OH:19])=[O:18]

Participants

5

Reactant 1

HCID 15517691HCID 15517691, compound

Product 1

HCID 9801884HCID 9801884, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

The benzyl (S)-6-(benzyloxycarbonylamino)-2-((2-methyl-1-(3-phenylpropanoylamino)propyl)(hydroxyphosphinoyl)oxy)hexanoate (85 mg) obtained in the above step (c) was dissolved in a mixed solvent of dioxane (2.4 ml) and water (0.8 ml) and added with palladium hydroxide (45.8 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 24 hours. The reaction mixture was filtered with celite and the filtrate was concentrated. The residue was purified with HP-20 (Diaion, 10 cc, methanol:water=1:4 to 1:1) to obtain the title compound: (S)-6-amino-2-((2-methyl-1-(3-phenylpropanoylamino)propyl)(hydroxyphosphinoyl)oxy)hexanoic acid (25 mg, 45%) (a diastereoisomeric mixture of 1:1).

Workup

  1. filtrationThe reaction mixture was filtered with celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified with HP-20 (Diaion, 10 cc, methanol:water=1:4 to 1:1)

Sources & evidence

ORD record
ord-d118744286b141ccb28dd089dc5bede8
Source dataset
uspto-grants-2003_06
Patent number
US06576627B1

Reaction notes

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