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Diisopropylethylamine → 5-(S)-azidomethyl-3-[4'-(N-methoxyamino)carbonyl-3'-fluorophenyl]-oxazolidine-2-one

HRID 351875
Notes
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Reaction equation

HRID 351875 reaction equation
Cl.[CH3:2][O:3][NH2:4].[N:5]([CH2:8][C@H:9]1[O:13][C:12](=[O:14])[N:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21](OC3C(F)=C(F)C(F)=C(F)C=3F)=[O:22])=[C:17]([F:35])[CH:16]=2)[CH2:10]1)=[N+:6]=[N-:7].C(N(C(C)C)CC)(C)C>C1COCC1>[N:5]([CH2:8][C@H:9]1[O:13][C:12](=[O:14])[N:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([NH:4][O:3][CH3:2])=[O:22])=[C:17]([F:35])[CH:16]=2)[CH2:10]1)=[N+:6]=[N-:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 229662165-(S)-Azidomethyl-3-[4'-(pentafluorophenoxy)carbonyl-3'-fluorophenyl]-oxazolidine-2-one

Product 1

HCID 229662155-(S)-azidomethyl-3-[4'-(N-methoxyamino)carbonyl-3'-fluorophenyl]-oxazolidine-2-oneYield 83.3%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

N-Methoxyamine hydrochloride (123 mg, 1.5 mmol) was added to a solution of 5-(S)-azidomethyl-3-[4′-(pentafluorophenoxy)carbonyl-3′-fluorophenyl]-oxazolidine-2-one (600 mg, 1.3 mmol) and diisopropylethylamine (0.26 ml, 1.5 mmol) in THF (8 ml), and the mixture stirred overnight at r.t. Solvent was removed under vacuum, and ethyl acetate with 3% aq. citric acid added. Organic layer was washed twice with 3% citric acid, brine, and dried (Na2SO4). Solvent was removed under vacuum, and the crude material crystallized from ethanol-ether to give a white crystalline product (335 mg, 83%). HPLC Rt=4.8. MS (m/z): [M+H]+=310.

Workup

  1. customSolvent was removed under vacuum, and ethyl acetate with 3% aq. citric acid
  2. additionadded
  3. washOrganic layer was washed twice with 3% citric acid, brine
  4. dry with materialdried (Na2SO4)
  5. customSolvent was removed under vacuum
  6. customthe crude material crystallized from ethanol-ether

Sources & evidence

ORD record
ord-5a53b491230843f3b00c45f05d7b44b4
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06743811B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes