Citric Acid → 5-(S)-Azidomethyl-3-[4'-(pentafluorophenoxy)carbonyl-3'-fluorophenyl]-oxazolidine-2-one

HRID 351874Notes

Reaction equation

HRID 351874 reaction equation
F[C:2](F)(F)[C:3]([O:5][C:6]1[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]([F:15])[C:7]=1[F:16])=[O:4].[N:19]([CH2:22][C@H:23]1[O:27][C:26](=[O:28])[N:25]([C:29]2[CH:34]=[CH:33]C(C(O)=O)=[C:31]([F:38])[CH:30]=2)[CH2:24]1)=[N+:20]=[N-:21].N1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C.C(OCC)(=O)C>[N:19]([CH2:22][C@H:23]1[O:27][C:26](=[O:28])[N:25]([C:29]2[CH:34]=[CH:33][C:2]([C:3]([O:5][C:6]3[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]([F:15])[C:7]=3[F:16])=[O:4])=[C:31]([F:38])[CH:30]=2)[CH2:24]1)=[N+:20]=[N-:21]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 1049PyridineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 229662095-(S)-azidomethyl-3-(4'-carboxy-3'-fluorophenyl)oxazolidine-2-one

Product 1

HCID 229662165-(S)-Azidomethyl-3-[4'-(pentafluorophenoxy)carbonyl-3'-fluorophenyl]-oxazolidine-2-oneYield 90.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pentafluorophenyl trifluoroacetate (2.2 ml, 12.9 mmol) was added dropwise with stirring to a solution of 5-(S)-azidomethyl-3-[4′-carboxy-3′-fluorophenyl]oxazolidine-2-one (3.0 g, 10.7 mmol; prepared as described in Example 3) and pyridine (3.5 ml, 42.8 mmol) in DMF (10 ml). The mixture was stirred at r.t. for 2.5 h, and ethyl acetate with 3% aq. citric acid added. Organic layer was washed twice with 3% citric acid, brine, and dried (Na2SO4). The crude material was washed with ether-hexanes to afford a white crystalline product (4.3 g, 90%). HPLC Rt=7.1. MS (m/z): [M+H]+=447.

Workup

  1. washOrganic layer was washed twice with 3% citric acid, brine
  2. dry with materialdried (Na2SO4)
  3. washThe crude material was washed with ether-hexanes

Sources & evidence

ORD record
ord-1b13c256c3b34560ac6989046b746711
Source dataset
uspto-grants-2004_06
Patent number
US06743811B2

Reaction notes

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