HCID 178444619, compound → HCID 178444621, compound

HRID 1396945Notes

Reaction equation

HRID 1396945 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:9][C:10]([C@@H:12]2[CH2:16][CH2:15][N:14](C([O-])=O)[N:13]2[C:20](=[O:39])[C@@H:21]([CH2:27][N:28]([CH:37]=[O:38])[O:29]CC2C=CC=CC=2)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:11])=[N+:6]([O-:8])[CH:7]=1>CO.[OH-].[OH-].[Pd+2]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:9][C:10]([C@@H:12]2[CH2:16][CH2:15][NH:14][N:13]2[C:20](=[O:39])[C@@H:21]([CH2:27][N:28]([CH:37]=[O:38])[OH:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:11])=[N+:6]([O-:8])[CH:7]=1

Participants

4

Reactant 1

HCID 178444619HCID 178444619, compound

Product 1

HCID 178444621HCID 178444621, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a 50 mL round-bottomed flask was added (3S)-3-{[(5-fluoro-1-oxido-2-pyridinyl)amino]carbonyl}-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl]-1-pyrazolidinecarboxylate (103 mg, 0.162 mmol) in methanol (3 ml), followed by Pearlman's catalyst (10 mg). The mixture was stirred under a balloon of H2 for 37 min, and the catalyst was filtered off. The filtrate was concentrated and the residue was purified by RP-HPLC to provide (3S)—N-(5-fluoro-1-oxido-2-pyridinyl)-2-((2R)-2-{[formyl(hydroxy)amino]methyl}heptanoyl)-3-pyrazolidinecarboxamide (49 mg, 73%). LCMS: (M+H)+: 412.0. 1H NMR (400 MHz, METHANOL-d4) δ ppm 0.76-0.98 (m, 3H) 1.26-1.46 (m, 6H) 1.48-1.57 (m, 1H) 1.63-1.77 (m, 1H) 2.30-2.44 (m, 1H) 2.46-2.59 (m, 1H) 2.91 (td, J=10.67, 6.44 Hz, 1H) 3.20-3.29 (m, 1H) 3.52 (dd, J=13.77, 4.42 Hz, 1H) 3.77-3.96 (m, 2H) 4.81-4.88 (m, 1H) 7.47 (ddd, J=9.66, 7.14, 2.65 Hz, 1H) 7.90 (s, 1H) 8.40-8.61 (m, 2H)

Workup

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

Sources & evidence

ORD record
ord-78d61e3ddf534102ada36dfb849c54b2
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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