Acetic Acid → (S)-(-)-N-[[3-[4-[1-(4-Oxo-2-thiazolinyl)-4-piperidinyl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 277834Notes

Reaction equation

HRID 277834 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[C:9]([F:19])[CH:8]=2)[CH2:5][C@H:4]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:3]1.[S:25]([CH2:28][C:29]([O:31]C)=O)[C:26]#[N:27].C(O)(=O)C>C(O)C.C(Cl)Cl>[O:31]=[C:29]1[CH2:28][S:25][C:26]([N:16]2[CH2:15][CH2:14][CH:13]([C:10]3[CH:11]=[CH:12][C:7]([N:6]4[CH2:5][C@H:4]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:3][C:2]4=[O:1])=[CH:8][C:9]=3[F:19])[CH2:18][CH2:17]2)=[N:27]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 12718Methyl 2-thiocyanatoacetateHCID 15887422(S)-(-)-N-[[2-Oxo-3-[4-(4-piperidinyl)-3-fluorophenyl]-5-oxazolidinyl]methyl]acetamide

Product 1

HCID 69765548(S)-(-)-N-[[3-[4-[1-(4-Oxo-2-thiazolinyl)-4-piperidinyl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (S)-(−)-N-[[2-oxo-3-[4-(4-piperidinyl)-3-fluorophenyl]-5-oxazolidinyl]methyl]acetamide (EXAMPLE 20, 310 mg), methyl thiocyanatoacetate (121 mg, Bull. Chem. Soc. Jpn. 1972, 45(5), 1507) and glacial acetic acid (55 mg) in absolute ethanol (5 mL) is stirred at reflux under N2 for 4 hrs and then cooled to ambient temperature, diluted with methylene chloride (45 mL), washed with water (2×15 mL) and saline (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is chromatographed on silica gel (230-400 mesh, 45 g), eluting with methanol/methylene chloride (4/96), and those fractions with an Rf=0.47 by TLC (methanol/chloroform, 10/90) are pooled and concentrated to give the title compound, mp 222-224° C. (decomp.).

Workup

  1. temperatureat reflux under N2 for 4 hrs
  2. washwashed with water (2×15 mL) and saline (20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is chromatographed on silica gel (230-400 mesh, 45 g)
  6. washeluting with methanol/methylene chloride (4/96)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ce37bf93e3de47fe94af787c4245c83e
Source dataset
uspto-grants-2002_03
Patent number
US06358942B1

Reaction notes

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