Methyl iodide → 5-(S)-Azidomethyl-3-[4'-methylthio-3'-fluorophenyl]oxazolidine-2-one

HRID 2305671Notes

Reaction equation

HRID 2305671 reaction equation
C(O)(C(F)(F)F)=O.C([SiH](C(C)C)C(C)C)(C)C.[N:18]([CH2:21][C@H:22]1[O:26][C:25](=[O:27])[N:24]([C:28]2[CH:33]=[CH:32][C:31]([S:34][C:35](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[C:30]([F:54])[CH:29]=2)[CH2:23]1)=[N+:19]=[N-:20].IC.C(N(CC)CC)C>C(Cl)Cl>[N:18]([CH2:21][C@H:22]1[O:26][C:25](=[O:27])[N:24]([C:28]2[CH:33]=[CH:32][C:31]([S:34][CH3:35])=[C:30]([F:54])[CH:29]=2)[CH2:23]1)=[N+:19]=[N-:20]

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 138754Silane, tris(1-methylethyl)-HCID 229662215-(S)-azidomethyl-3-[4'-triphenylmethylthio-3'-fluorophenyl]-oxazolidine-2-one

Product 1

HCID 229662145-(S)-Azidomethyl-3-[4'-methylthio-3'-fluorophenyl]oxazolidine-2-oneYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5% TFA and 2.5% triisopropylsilane in DCM (4 ml) was added to 5-(S)-azidomethyl-3-[4′-triphenylmethylthio-3′-fluorophenyl]oxazolidine-2-one (0.250 g, 0.490 mmol; prepared as described above for Example 6), and the mixture stirred for 1 h at r.t. Solvent was removed under vacuum and the residue dissolved in DMF (2 ml). Iodomethane (0.046 ml, 0.735 mmol) was added followed by dropwise addition of triethylamine (0.136 ml, 0.979 mmol). The mixture was stirred at r.t. for 2 h, evaporated, and the residue purified by PTLC (50% ethyl acetate in DCM) to give the product as a white solid (0.124 g, 90%). MS (m/z): [M+H]+=283.

Workup

  1. customSolvent was removed under vacuum
  2. dissolutionthe residue dissolved in DMF (2 ml)
  3. stirringThe mixture was stirred at r.t. for 2 h
  4. customevaporated
  5. customthe residue purified by PTLC (50% ethyl acetate in DCM)

Sources & evidence

ORD record
ord-6038df2371b44c07a7122bbbd7584c4e
Source dataset
uspto-grants-2002_08
Patent number
US06441005B1

Reaction notes

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