Phenylmethyl (3S)-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl]-3-[(3-pyridazinylamino)carbonyl]-1-pyrazolidinecarboxylate → (3S)-2-((2R)-2-{[Formyl(hydroxy)amino]methyl}heptanoyl)-N-3-pyridazinyl-3-pyrazolidinecarboxamide

HRID 1396953Notes

Reaction equation

HRID 1396953 reaction equation
[CH:1]([N:3]([CH2:12][C@@H:13]([CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:14]([N:16]1[C@H:20]([C:21]([NH:23][C:24]2[N:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[O:22])[CH2:19][CH2:18][N:17]1C(OCC1C=CC=CC=1)=O)=[O:15])[O:4]CC1C=CC=CC=1)=[O:2]>CO.[OH-].[OH-].[Pd+2]>[CH:1]([N:3]([CH2:12][C@@H:13]([CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:14]([N:16]1[C@H:20]([C:21]([NH:23][C:24]2[N:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[O:22])[CH2:19][CH2:18][NH:17]1)=[O:15])[OH:4])=[O:2]

Participants

4

Reactant 1

HCID 86706386Phenylmethyl (3S)-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl]-3-[(3-pyridazinylamino)carbonyl]-1-pyrazolidinecarboxylate

Product 1

HCID 66546696(3S)-2-((2R)-2-{[Formyl(hydroxy)amino]methyl}heptanoyl)-N-3-pyridazinyl-3-pyrazolidinecarboxamideYield 34.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of phenylmethyl (3S)-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl]-3-[(3-pyridazinylamino) carbonyl]-1-pyrazolidinecarboxylate (460 mg, 0.764 mmol) in methanol (15 mL) was added Pd(OH)2/C (300 mg). The mixture was stirred under an H2 atmosphere for 2 h and the catalyst was filtered off. The filtrate was concentrated and the residue was purified by pre-HPLC to provide the titled compound (100 mg, 30%) as a yellowish solid. LCMS: (M+H)+: 379.2.

Workup

  1. filtrationthe catalyst was filtered off
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by pre-HPLC

Sources & evidence

ORD record
ord-5b153ab3220745cca3d438c503028214
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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