HCID 178523396, compound → HCID 178523982, compound

HRID 1396879Notes

Reaction equation

HRID 1396879 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:35][N:36]([CH:45]=[O:46])[O:37]CC2C=CC=CC=2)[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N+:19]=3[O-:24])=[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.[Pd]>[CH:1]1([CH2:6][C@H:7]([CH2:35][N:36]([CH:45]=[O:46])[OH:37])[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N+:19]=3[O-:24])=[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 178523396HCID 178523396, compound

Product 1

HCID 178523982HCID 178523982, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-{[(1-oxido-2-pyridinyl)amino]carbonyl}-1-pyrazolidine carboxylate (105 mg, 0.167 mmol) in methanol (10 ml) was added 10% palladium on carbon (17.75 mg, 0.017 mmol). The mixture was hydrogenated under balloon pressure for 72 h and then filtered. The mixture was purified by reverse-phase HPLC to yield (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-(1-oxido-2-pyridinyl)-3-pyrazolidinecarboxamide (35 mg, 0.086 mmol, 52% yield). LC/MS: (M+H)+: 06.4. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.07-1.28 (m, 3H) 1.39-1.69 (m, 5H) 1.69-1.84 (m, 2H) 1.84-2.02 (m, 2H) 2.29-2.46 (m, 1H) 2.46-2.64 (m, 1H) 2.84-3.00 (m, 1H) 3.19-3.31 (m, 1H) 3.46-3.61 (m, 1H) 3.76-3.90 (m, 1H) 3.93-4.14 (m, 1H) 4.76-4.87 (m, 1H) 7.10-7.34 (m, 1H) 7.58 (t, J=8.08 Hz, 1H) 7.90 (s, 1H) 8.34 (d, J=6.32 Hz, 1H) 8.49 (dd, J=8.59, 1.52 Hz, 1H).

Workup

  1. filtrationfiltered
  2. customThe mixture was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-b3ab8b9c4d9b417f848a9faf29e42d65
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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