HCID 178445896, compound → HCID 178445908, compound

HRID 1396957Notes

Reaction equation

HRID 1396957 reaction equation
[CH:1]([N:3]([CH2:12][C@@H:13]([CH2:41][CH2:42][CH2:43][CH3:44])[C:14]([N:16]1[C@H:20]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N+:25]=2[O-:30])=[O:22])[CH2:19][CH2:18][N:17]1C(OCC1C=CC=CC=1)=O)=[O:15])[O:4]CC1C=CC=CC=1)=[O:2]>CCO.[OH-].[OH-].[Pd+2]>[CH:1]([N:3]([CH2:12][C@@H:13]([CH2:41][CH2:42][CH2:43][CH3:44])[C:14]([N:16]1[C@H:20]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N+:25]=2[O-:30])=[O:22])[CH2:19][CH2:18][NH:17]1)=[O:15])[OH:4])=[O:2]

Participants

4

Reactant 1

HCID 178445896HCID 178445896, compound

Product 1

HCID 178445908HCID 178445908, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of phenylmethyl (3S)-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)hexanoyl]-3-{[(1-oxido-2-pyridinyl)amino]carbonyl}-1-pyrazolidinecarboxylate (85 mg, 0.14 mmol) in EtOH (15 mL) was added Pd(OH)2/C (30 mg). The mixture was degassed and placed under H2 atmosphere for 1 h at rt. The catalyst was filtered off and the filtrate was concentrated. The residue was purified by pre-HPLC to provide the titled compound (22 mg, 40%). LCMS: (M+H)+: 380.2.

Workup

  1. customThe mixture was degassed
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by pre-HPLC

Sources & evidence

ORD record
ord-f7956d69853b491cab089deb8976b383
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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