HCID 131732106, compound → HCID 88948357, compound

HRID 1396958Notes

Reaction equation

HRID 1396958 reaction equation
[CH:1]([N:3]([CH2:12][C@@H:13]([CH2:40][CH2:41][CH2:42][CH3:43])[C:14]([N:16]1[C@H:20]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][N:27]=[CH:26][N:25]=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]>C(O)C.[OH-].[OH-].[Pd+2]>[CH:1]([N:3]([CH2:12][C@@H:13]([CH2:40][CH2:41][CH2:42][CH3:43])[C:14]([N:16]1[C@H:20]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][N:27]=[CH:26][N:25]=2)=[O:22])[CH2:19][CH2:18][NH:17]1)=[O:15])[OH:4])=[O:2]

Participants

4

Reactant 1

HCID 131732106HCID 131732106, compound

Product 1

HCID 88948357HCID 88948357, compoundYield 80.7%

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-[(4-pyrimidinylamino)carbonyl]-1-pyrazolidinecarboxylate (80 mg, 0.136 mmol) in ethanol (30 mL) was added Pd(OH)2/C (40 mg). The mixture was stirred under an H2 atmosphere for 1 h and the catalyst was filtered off. The filtrate was concentrated and the residue was purified by pre-HPLC to provide the title compound (40 mg, 70%). LCMS: (M+H)+: 365.2.

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-f0428c131e884be48b3c7315510bc131
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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