Phenylmethyl (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-3-({[4-(2-pyridinyl)-2-pyrimidinyl]amino}carbonyl)-1-pyrazolidinecarboxylate → (3S)-2-((2R)-3-Cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-[4-(2-pyridinyl)-2-pyrimidinyl]-3-pyrazolidinecarboxamide

HRID 1396965Notes

Reaction equation

HRID 1396965 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:40][N:41]([CH:43]=[O:44])[OH:42])[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[N:23]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[CH:21]=[CH:20][N:19]=3)=[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.[OH-].[OH-].[Pd+2]>[CH:1]1([CH2:6][C@H:7]([CH2:40][N:41]([CH:43]=[O:44])[OH:42])[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[N:23]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[CH:21]=[CH:20][N:19]=3)=[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 131732109Phenylmethyl (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-3-({[4-(2-pyridinyl)-2-pyrimidinyl]amino}carbonyl)-1-pyrazolidinecarboxylate

Product 1

HCID 88923395(3S)-2-((2R)-3-Cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-[4-(2-pyridinyl)-2-pyrimidinyl]-3-pyrazolidinecarboxamideYield 56.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of phenylmethyl (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-3-({[4-(2-pyridinyl)-2-pyrimidinyl]amino}carbonyl)-1-pyrazolidinecarboxylate (32 mg, 0.053 mmol) in methanol (3 mL) was added Pd(OH)2/C (7 mg). The mixture was degassed and then stirred under an H2 atmosphere for 2 h at rt. The catalyst was filtered off. The filtrate was concentrated and the residue was purified by pre-HPLC to provide the title compound (14 mg, 56%). LCMS: (M+H)+: 468.2.

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-6ad43ea07a8b433daa7410200c81bd77
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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