Sodium Azide → 5-(S)-Azidomethyloxazolidine-2-one

HRID 412499

Reaction equation

HRID 412499 reaction equation
Cl[CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[NH:5][CH2:4]1.[N-:9]=[N+:10]=[N-:11].[Na+].[N-]=[N+]=[N-].C([N+](CCCC)(CCCC)CCCC)CCC>CC(C)=O.CN(C)C=O>[N:9]([CH2:2][C@H:3]1[O:7][C:6](=[O:8])[NH:5][CH2:4]1)=[N+:10]=[N-:11]

Participants

6

Reactant 3

HCID 33557Sodium Azide2×HCID 57432321-Butanaminium, N,N,N-tributyl-, azideHCID 7058041(5R)-5-(chloromethyl)-1,3-oxazolidin-2-one

Product 1

HCID 229773185-(S)-Azidomethyloxazolidine-2-one

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

5-(R)-Chloromethyloxazolidine-2-one (prepared according to [Danielmeier et al. Efficient Pathways to (R)- and (S)-hydroxymethyl-2-oxazolidinone and some derivatives. Tetrahedron: Asymmetry. 1995, vol. 6, pp. 1181-1190] (5 mmol) is reacted with sodium azide (7-10 mmol) in acetone (ca. 40-50 mL) at r.t. for ca. 24 h (until the reaction is completed). Solids are filtered off, and supernatant evaporated under vacuum to afford the product which is immediately used for the next step. Optionally, the synthesis is performed in dry N,N-dimethylformamide under inert atmosphere with sodium azide (5-10 mmol) or tetrabutylammonium azide (5-10 mmol), and the resulting solution of the crude 5-(S)-azidomethyloxazolidine-2-one is employed for the next step without solvent removal.

Workup

  1. filtrationSolids are filtered off
  2. customsupernatant evaporated under vacuum
  3. customto afford the product which
  4. customthe resulting solution of the crude 5-(S)-azidomethyloxazolidine-2-one is employed for the next step without solvent removal

Sources & evidence

ORD record
ord-e7a6bcfd0c644788b68bfc57859c832d
Source dataset
uspto-grants-2003_05
Patent number
US06562844B2

Linked notes

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