1,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamine → N-[(5S)-3-(3-Fluoro-4-(4-pyrimidin-2-ylthiomethylimidazol-1-yl)phenyl)-2-oxooxazolidin-5-ylmethyl]acetamide

HRID 2299015Notes

Reaction equation

HRID 2299015 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]O)[N:10]=[CH:9]1.[NH:26]1[CH:31]=[CH:30][CH:29]=[N:28][C:27]1=[S:32].C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C>C(#N)C>[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][S:32][C:27]2[N:28]=[CH:29][CH:30]=[CH:31][N:26]=2)[N:10]=[CH:9]1

Participants

5

Reactant 3

HCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 15504892-MercaptopyrimidineHCID 10760118N-[(5S)-3-(3-Fluoro-4-(4-hydroxymethylimidazol-1-yl)phenyl)-2-oxooxazolidin-5-yl-methyl]acetamide

Product 1

HCID 70155434N-[(5S)-3-(3-Fluoro-4-(4-pyrimidin-2-ylthiomethylimidazol-1-yl)phenyl)-2-oxooxazolidin-5-ylmethyl]acetamideYield 92.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-[(5S)-3-(3-Fluoro-4-(4-hydroxymethylimidazol-1-yl)phenyl)-2-oxooxazolidin-5-yl-methyl]acetamide (174 mg, 0.5 mM) and pyrimidine-2-thione (112 mg, 1 mM) were suspended in dry acetonitrile (20 ml), and N,N-dimethylformamide dineopentyl acetal (462 mg, 2 mM) added. The mixture was heated to reflux for 6 hours giving a solution. Solvent was evaporated, the residue dissolved in dichloromethane, and subjected to mplc on silica, eluting with a gradient increasing in polarity from 0 to 20% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the title product (204 mg) as a gum.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 hours
  3. customgiving a solution
  4. customSolvent was evaporated
  5. dissolutionthe residue dissolved in dichloromethane
  6. washeluting with
  7. temperaturea gradient increasing in polarity from 0 to 20% methanol in dichloromethane
  8. customevaporated

Sources & evidence

ORD record
ord-a3f5b4fc391245519552ebf496e81775
Source dataset
uspto-grants-2002_12
Patent number
US06495551B1

Reaction notes

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