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

HRID 1979282

反応式

HRID 1979282 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-59df81ced1b04f56b198111e95c396a4
出典データセット
uspto-grants-2001_05
特許番号
US06239152B1

関連ノート

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