HCID 86588565, compound → HCID 12989038, compound

HRID 1368884Notes

Reaction equation

HRID 1368884 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([O:27][P:28]([CH:38]([NH:42][C:43](=[O:53])[CH2:44][CH2:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[CH:39]([CH3:41])[CH3:40])([O:30]CC1C=CC=CC=1)=[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:38]([NH:42][C:43](=[O:53])[CH2:44][CH2:45][CH2:46][C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1)[CH:39]([CH3:41])[CH3:40])([OH:30])=[O:29])[C:17]([OH:19])=[O:18]

Participants

5

Reactant 1

HCID 86588565HCID 86588565, compound

Product 1

HCID 12989038HCID 12989038, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

The benzyl (S)-6-benzyloxycarbonylamino-2-((2-methyl-1-(4-phenylbutanoylamino)propyl)(benzyloxyphosphinoyl)oxy)hexanoate (43.9 mg) obtained in the above step (f) was dissolved in a mixed solvent of dioxane and water (3:1) (439 ml), and the solution was added with palladium hydroxide (8.8 mg) and stirred under a hydrogen atmosphere at room temperature for 18 hours. The reaction mixture was filtered with celite, and the filtrate was concentrated under reduced pressure. The residue was purified by HP-20 (Diaion, 5 g, water to methanol) to obtain the title compound: (S)-6-amino-2-(2-methyl-1-(4-phenylbutanoylamino)propyl(hydroxyphosphinoyl)oxy)hexanoic acid (17.5 mg, 70%, a diastereoisomeric mixture of 1:1).

Workup

  1. filtrationThe reaction mixture was filtered with celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by HP-20 (Diaion, 5 g, water to methanol)

Sources & evidence

ORD record
ord-988df74e41af46149872d2e18134d84f
Source dataset
uspto-grants-2003_06
Patent number
US06576627B1

Reaction notes

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