4-{4-[(5S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluorophenoxymethyl}-4-hydroxy-piperidine-1-carboxylic acid benzylester → HCID 11164924, compound

HRID 2387573Notes

Reaction equation

HRID 2387573 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][C:14]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:30][C@H:29]([CH2:31][NH:32][C:33](=[O:35])[CH3:34])[O:28][C:27]3=[O:36])=[CH:22][C:21]=2[F:37])([OH:17])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[F:37][C:21]1[CH:22]=[C:23]([N:26]2[CH2:30][C@H:29]([CH2:31][NH:32][C:33](=[O:35])[CH3:34])[O:28][C:27]2=[O:36])[CH:24]=[CH:25][C:20]=1[O:19][CH2:18][C:14]1([OH:17])[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1

Participants

5

Reactant 1

HCID 667727114-{4-[(5S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluorophenoxymethyl}-4-hydroxy-piperidine-1-carboxylic acid benzylester

Product 1

HCID 11164924HCID 11164924, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
40 °C

Procedure

A suspension of 31 g 4-{4-[(5S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluorophenoxymethyl}-4-hydroxy-piperidine-1-carboxylic acid benzylester (MW: 515.54 60.13 mmol) and 2.5 g of palladium 10% on activated carbon in 310 ml methanol and 150 ml ethyl acetate was stirred under hydrogen for 4 hrs. The reaction was monitored by TLC (ethyl acetate). The reaction slurry was diluted with 300 ml methanol, warmed to 40° C., and the catalyst filtered off using a glass fibre filter paper. The filtrate was concentrated to 150 ml, diluted with 300 ml ethyl acetate and concentrated again to 200 ml. 200 ml of diethyl ether were added, and the suspension was cooled to 0° C. under stirring. The solid was collected and dried. Yield: 21.6-g, 94.3%. MS: 382.6 (M+H)+, Method ESI+.

Workup

  1. filtrationthe catalyst filtered off
  2. filtrationfilter paper
  3. concentrationThe filtrate was concentrated to 150 ml
  4. additiondiluted with 300 ml ethyl acetate
  5. concentrationconcentrated again to 200 ml
  6. addition200 ml of diethyl ether were added
  7. temperaturethe suspension was cooled to 0° C.
  8. stirringunder stirring
  9. customThe solid was collected
  10. customdried

Sources & evidence

ORD record
ord-eec311046fc444518eeb18aaf3d03600
Source dataset
uspto-grants-2012_09
Patent number
US08268812B2

Reaction notes

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