HCID 22717928, compound → HCID 9887892, compound

HRID 1368880Notes

Reaction equation

HRID 1368880 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:20][P:21]([CH:24]([NH:28][C:29](=[O:38])[CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH:25]([CH3:27])[CH3:26])([OH:23])=[O:22])[C:17]([OH:19])=[O:18])=O)C1C=CC=CC=1>O1CCOCC1.O.[OH-].[Pd+2].[OH-]>[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:20][P:21]([CH:24]([NH:28][C:29](=[O:38])[CH2:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH:25]([CH3:26])[CH3:27])([OH:23])=[O:22])[C:17]([OH:19])=[O:18]

Participants

5

Reactant 1

HCID 22717928HCID 22717928, compound

Product 1

HCID 9887892HCID 9887892, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

The crude 6-benzyloxycarbonylamino-2-((2-methyl-1-(3-phenylpropanoylamino)propyl)hydroxyphosphinoyl)methylhexanoic acid (181 mg) obtained in the above step (g) was dissolved in a mixed solvent of dioxane and water (1:1) (4 ml). The solution was added with palladium hydroxide (37 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 4 hours. The reaction mixture was filtered with celite and the filtrate was concentrated. The residue was purified with HP-20 (Diaion, 20 cc, methanol:water=1:9 to acetone:water=1:1) to obtain the title compound: 6-amino-2-((2-methyl-1-(3-phenylpropanoylamino)propyl)hydroxyphosphinoyl)methylhexanoic acid (74 mg, 54%) (a diastereoisomeric mixture of 3:1).

Workup

  1. filtrationThe reaction mixture was filtered with celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified with HP-20 (Diaion, 20 cc, methanol:water=1:9 to acetone:water=1:1)

Sources & evidence

ORD record
ord-3824868c098f4e09a5336aa41d1c2744
Source dataset
uspto-grants-2003_06
Patent number
US06576627B1

Reaction notes

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