HCID 86730272, compound → HCID 86730270, compound

HRID 1850218Notes

Reaction equation

HRID 1850218 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C@@H:17]([NH:19][C:20]2[N:25]=[C:24]([N:26]3[C@@H:30]([CH:31]([CH3:33])[CH3:32])[CH2:29][O:28][C:27]3=[O:34])[CH:23]=[CH:22][N:21]=2)[CH3:18])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH:31]([C@H:30]1[CH2:29][O:28][C:27](=[O:34])[N:26]1[C:24]1[CH:23]=[CH:22][N:21]=[C:20]([NH:19][C@H:17]([CH:14]2[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]2)[CH3:18])[N:25]=1)([CH3:32])[CH3:33]

Participants

4

Reactant 1

HCID 86730272HCID 86730272, compound

Product 1

HCID 86730270HCID 86730270, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-{(S)-1-[4-((S)-4-Isopropyl-2-oxo-oxazolidin-3-yl)-pyrimidin-2-ylamino]-ethyl}-piperidine-1-carboxylic acid benzyl ester (22 mg) in methanol (5 mL) was added palladium hydroxide on carbon (7 mg, 0.05 mmol). The reaction was then stirred at room temperature for 16 hours. The reaction is then filtered and then concentrated under vacuum. The crude material was then purified using reverse phase C18 ODB column water-acetonitrile 0.1% TFA modifier to give (S)-4-isopropyl-3-[2-((S)-1-piperidin-4-yl-ethylamino)-pyrimidin-4-yl]-oxazolidin-2-one (11 mg) in 70% yield.

Workup

  1. filtrationThe reaction is then filtered
  2. concentrationconcentrated under vacuum
  3. customThe crude material was then purified

Sources & evidence

ORD record
ord-a7ab7b86a5984181b9457e16e05d2483
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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