2-Furancarboxylic acid → N-[(5S)-3-(3-Fluoro-4-(4-(2-Furoyloxymethyl)imidazol-1-yl)phenyl)-2-oxooxazolidin-5-ylmethyl]acetamide

HRID 2299021Notes

Reaction equation

HRID 2299021 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:15]2[CH2:19][C@H:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][C:16]2=[O:25])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH2:13][OH:14])[N:10]=[CH:9]1.[O:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[C:31](O)=[O:32].C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([N:15]2[CH2:19][C@H:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][C:16]2=[O:25])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH2:13][O:14][C:31]([C:27]2[O:26][CH:30]=[CH:29][CH:28]=2)=[O:32])[N:10]=[CH:9]1

Participants

5

Reactant 3

HCID 69192-Furancarboxylic acidHCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 10760118N-[(5S)-3-(3-Fluoro-4-(4-hydroxymethylimidazol-1-yl)phenyl)-2-oxooxazolidin-5-yl-methyl]acetamide

Product 1

HCID 11762014N-[(5S)-3-(3-Fluoro-4-(4-(2-Furoyloxymethyl)imidazol-1-yl)phenyl)-2-oxooxazolidin-5-ylmethyl]acetamideYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[(5S)-3-(3-Fluoro-4-(4-hydroxymethylimidazol-1-yl)phenyl)-2-oxooxazolidin-5-yl-methyl]acetamide (174 mg, 0.5 mM) and furan-2-carboxylic acid (168 mg, 1.5 mM) were suspended in dry dichloromethane (20 ml) under argon, and N,N-dimethylformamide dineopentyl acetal (462 mg, 2 mM) added. The mixture was stirred at ambient temperature for 48 hours giving a solution. The mixture was diluted with an equal volume of dichworomethane, and washed with sufficent 5% aqueous sodium bicarbonate to remove all acids. The organic phase was dried over magnesium sulfate, evaporated, and the residue dissolved in dichloromethane and chromatographed on a 5 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 10% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the title product (184 mg).

Workup

  1. customgiving a solution
  2. additionThe mixture was diluted with an equal volume of dichworomethane
  3. washwashed with sufficent 5% aqueous sodium bicarbonate
  4. customto remove all acids
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customevaporated
  7. dissolutionthe residue dissolved in dichloromethane
  8. customchromatographed on a 5 g silica Mega Bond Elut® column
  9. washeluting with a gradient
  10. temperatureincreasing in polarity from 0 to 10% methanol in dichloromethane
  11. customevaporated

Sources & evidence

ORD record
ord-f3b4378a5b90441095685290cc93791b
Source dataset
uspto-grants-2002_12
Patent number
US06495551B1

Reaction notes

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