HCID 15887424, compound → HCID 54070724, compound

HRID 1740159Notes

Reaction equation

HRID 1740159 reaction equation
C([O:8][CH2:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[C:23]([F:24])=[CH:22][C:21]([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:20][C:19]=2[F:36])[CH2:14][CH2:13]1)=[O:11])C1C=CC=CC=1>CO.[Pd]>[OH:8][CH2:9][C:10]([N:12]1[CH2:13][CH2:14][CH:15]([C:18]2[C:19]([F:36])=[CH:20][C:21]([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:22][C:23]=2[F:24])[CH2:16][CH2:17]1)=[O:11]

Participants

4

Reactant 1

HCID 15887424HCID 15887424, compound

Product 1

HCID 54070724HCID 54070724, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (S)-(-)-N-[[3-[4-[1-[(benzyloxy)acetyl]-4-piperidinyl]-3,5-difluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (EXAMPLE 36, 207 mg) and 10% palladium-on-carbon (100 mg) in methanol (9 mL) is shaken on a Parr apparatus under a hydrogen atmosphere at 40 psi for 20 hours, the catalyst is removed by filtration through Celite and the filtrate is concentrated under reduced pressure to give the crude product which is chromatographed on silica gel (230-400 mesh, 20 g), eluting with a gradient of methanol/methylene chloride (5/95-10/90). Pooling and concentration of those fractions with an Rf =0.26 by TLC (methanol/chloroform, 10/90) and recrystallization from methylene chloride/diethyl ether gives the title compound, NMR (CDCl3, 400 MHz) 7.07, 6.80, 4.78, 4.69, 4.18, 3.99, 3.74, 3.63, 3.60, 3.16, 3.06, 2.90, 2.72, 2.00, 1.97, 1.75 δ.

Workup

  1. customthe catalyst is removed by filtration through Celite
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customto give the crude product which
  4. customis chromatographed on silica gel (230-400 mesh, 20 g)
  5. washeluting with a gradient of methanol/methylene chloride (5/95-10/90)
  6. customPooling and concentration of those fractions with an Rf =0.26 by TLC (methanol/chloroform, 10/90) and recrystallization from methylene chloride/diethyl ether

Sources & evidence

ORD record
ord-f8a93ab0c1c94eb7864f92c017314258
Source dataset
uspto-grants-1999_10
Patent number
US05968962

Reaction notes

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