Ethyl Acetate → (3R)3-{4-[(5S)-5-(Acetylaminomethyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenylamino}-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester

HRID 2193531Notes

Reaction equation

HRID 2193531 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([N:13]([C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH2:34][C@H:33]([CH2:35][N:36]=[N+]=[N-])[O:32][C:31]3=[O:39])=[CH:26][C:25]=2[F:40])C(OCC2C=CC=CC=2)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:41](OCC)(=[O:43])[CH3:42]>[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH2:34][C@H:33]([CH2:35][NH:36][C:41](=[O:43])[CH3:42])[O:32][C:31]3=[O:39])=[CH:26][C:25]=2[F:40])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 86597763(3R)-3-{[4-{(5R)-5-Azidomethyl-2-oxo-oxazolidin-3-yl}-2-fluoro-phenyl]-benzyloxycarbonyl-amino}-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester

Product 1

HCID 67274345(3R)3-{4-[(5S)-5-(Acetylaminomethyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenylamino}-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a stirred solution of 4.2 g of (3R)-3-{[4-{(5R)-5-azidomethyl-2-oxo-oxazolidin-3-yl}-2-fluoro-phenyl]-benzyl-oxycarbonyl-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester (7.3 mmol) in 50 ml ethyl acetate were added 400 mg of Pd/C 10% and the mixture was stirred under hydrogen over night. The reaction was controlled by TLC. The Pd/C was filtered, the filtrate evaporated to dryness. The residue was dissolved in 5 ml acetic acid and 2 ml acetic anhydride was added. The reaction was stirred at rt for 2 hrs and monitored by TLC. The solvents were evaporated, the residue dissolved in ethyl acetate, washed with water and brine, dried over Mg sulfate, filtered and the filtrate evaporated to dryness.

Workup

  1. filtrationThe Pd/C was filtered
  2. customthe filtrate evaporated to dryness
  3. dissolutionThe residue was dissolved in 5 ml acetic acid
  4. addition2 ml acetic anhydride was added
  5. stirringThe reaction was stirred at rt for 2 hrs
  6. customThe solvents were evaporated
  7. dissolutionthe residue dissolved in ethyl acetate
  8. washwashed with water and brine
  9. dry with materialdried over Mg sulfate
  10. filtrationfiltered
  11. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-9234c54315814ceda3c6c9025ea9c715
Source dataset
uspto-grants-2012_12
Patent number
US08329908B2

Reaction notes

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