3-{4-[(5S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester → HCID 57754804, compound

HRID 2279670Notes

Reaction equation

HRID 2279670 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][C:13]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:29][C@H:28]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[O:27][C:26]3=[O:35])=[CH:21][C:20]=2[F:36])([OH:16])[CH2:12]1)=O)C1C=CC=CC=1>[Pd].C(OCC)(=O)C.CO>[F:36][C:20]1[CH:21]=[C:22]([N:25]2[CH2:29][C@H:28]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[O:27][C:26]2=[O:35])[CH:23]=[CH:24][C:19]=1[O:18][CH2:17][C:13]1([OH:16])[CH2:14][CH2:15][NH:11][CH2:12]1

Participants

4

Reactant 1

HCID 672794053-{4-[(5S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

Product 1

HCID 57754804HCID 57754804, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A suspension of 660 mg 3-{4-[(5S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester (MW: 501.51, 1.31 mmol) and 20 mg palladium 10% on activated carbon in 20 ml of a 1/1 ethyl acetate/methanol mixture was stirred for twelve hours under hydrogen. The catalyst was filtered on a glass fiber filter paper and the filtrate evaporated under reduced pressure to afford a colorless oil. Yield: 400 mg, 83.2%. MS: 368.4 (M+H)+, Method ESI+.

Workup

  1. filtrationThe catalyst was filtered on a glass fiber
  2. filtrationfilter paper
  3. customthe filtrate evaporated under reduced pressure
  4. customto afford a colorless oil

Sources & evidence

ORD record
ord-9f9f287f9c2642e598d0eeedd505dab8
Source dataset
uspto-grants-2015_09
Patent number
US09133213B2

Reaction notes

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