Phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-{[(4-{[(phenylmethyl)oxy]carbonyl}phenyl)amino]carbonyl}-1-pyrazolidinecarboxylate → 4-({[(3S)-2-((2R)-3-Cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-3-pyrazolidinyl]carbonyl}amino)benzoic acid

HRID 1396960Notes

Reaction equation

HRID 1396960 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:44][N:45]([CH:54]=[O:55])[O:46]CC2C=CC=CC=2)[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([O:26]CC4C=CC=CC=4)=[O:25])=[CH:20][CH:19]=3)=[O:16])[CH2:13][CH2:12][N:11]2C(OCC2C=CC=CC=2)=O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[OH-].[OH-].[Pd+2]>[CH:1]1([CH2:6][C@H:7]([CH2:44][N:45]([CH:54]=[O:55])[OH:46])[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([OH:26])=[O:25])=[CH:20][CH:19]=3)=[O:16])[CH2:13][CH2:12][NH:11]2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 86706391Phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-{[(4-{[(phenylmethyl)oxy]carbonyl}phenyl)amino]carbonyl}-1-pyrazolidinecarboxylate

Product 1

HCID 867063924-({[(3S)-2-((2R)-3-Cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-3-pyrazolidinyl]carbonyl}amino)benzoic acidYield 52.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-{[(4-{[(phenylmethyl)oxy]carbonyl}phenyl)amino]carbonyl}-1-pyrazolidinecarboxylate (330 mg, 0.442 mmol) in methanol (20 mL) was added Pd(OH)2/C (330 mg). The mixture was stirred at rt under H2 atmosphere for 2 h. The catalyst was filtered off, the filtrate was concentrated under vacuum, and the residue was purified by preparative HPLC to provide the title compound (100 mg). LCMS: (M+H)+: 482.2.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under vacuum
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-824adcd2acfd4f1296a9ef288be1baa1
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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