HCID 53713463, compound → HCID 15549553, compound

HRID 266713Notes

Reaction equation

HRID 266713 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([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:5]=[C:6]([F:25])[C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:24])[CH2:15][O:16]CC2C=CC=CC=2)[CH2:10][CH2:9]1>CO>[F:25][C:6]1[CH:5]=[C:4]([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:3]=[C:2]([F:1])[C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:24])[CH2:15][OH:16])[CH2:10][CH2:9]1

Participants

3

Reactant 1

HCID 53713463HCID 53713463, compound

Product 1

HCID 15549553HCID 15549553, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Next, (S)-N-[[3-[3,5-difluoro-4-[4-(benzyloxyacetyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (3.84 g, 7.6 mmol) was dissolved in hot 10% EtOac/MeOH (150 mL). After degassing the solution three times with N2, the Pearlman's catalyst (384 mg, 10% by weight) was added. The solution was degassed again and then the atmosphere was replaced with H2. The reaction was stirred at room temperature for 4.5 hours. At this point, the reaction was found to be complete by TLC (10% MeOH/CHCl3, UV short wave). The solution was filtered through celite, washing the cake with EtOAc (250 mL). The filtrate was concentrated under reduced pressure to give a white solid. The material was chromatographed on silica gel (150 g), eluting with a gradient of 1-6, 10% MeOH in 10% CH3CN/CHCl3 to yield 3.078 g (98%) of (S)-N-[[3-[3,5-difluoro-4-[4-(hydroxyacetyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide as a white solid with a melting point of 160.5°-162.5° C.

Workup

  1. customAfter degassing the solution three times with N2
  2. additionthe Pearlman's catalyst (384 mg, 10% by weight) was added
  3. customThe solution was degassed again
  4. filtrationThe solution was filtered through celite
  5. washwashing the cake with EtOAc (250 mL)
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customto give a white solid
  8. customThe material was chromatographed on silica gel (150 g)
  9. washeluting with a gradient of 1-6, 10% MeOH in 10% CH3CN/CHCl3

Sources & evidence

ORD record
ord-8423941c7e3f4777854b15a9881725d5
Source dataset
uspto-grants-1997_07
Patent number
US05652238

Reaction notes

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