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

HRID 226221Notes

Reaction equation

HRID 226221 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 of 4-{4-[(5S)-5-(acetylaminomethyl)-2-oxo-oxazolidin-3-yl]-2-fluorophenoxymethyl}-4-hydroxypiperidin-1-carboxylic acid benzyl ester (MW: 515.54, 60.13 mmol) and 2.5 g of palladium (10% on activated carbon) in 310 ml of methanol and 150 ml of ethyl acetate was stirred for 4 h under a hydrogen atmosphere. The course of the reaction was monitored by TLC (ethyl acetate). The suspension was diluted with 300 ml of methanol, heated to 40° C., and the catalyst was filtered off through a fibreglass filter paper. The filtrate was concentrated to 150 ml, diluted with 300 ml of ethyl acetate and concentrated again to 200 ml. 200 ml of diethyl ether were added and the suspension was cooled, with stirring, to 0° C. The solid material was collected and dried. Yield: 21.6 g, 94.3%. MS: 382.6 (M+H)+, Method: ESI+.

Workup

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

Sources & evidence

ORD record
ord-ac39a78d41e24d9a9119329f3b873231
Source dataset
uspto-grants-2009_07
Patent number
US07557214B2

Reaction notes

Loading…