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

HRID 1861234

반응식

HRID 1861234 반응식
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]

참가 물질

6

반응물 3

HCID 33557Sodium Azide2회HCID 57432321-Butanaminium, N,N,N-tributyl-, azideHCID 7058041(5R)-5-(chloromethyl)-1,3-oxazolidin-2-one

생성물 1

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

시약·촉매·용매 2

HCID 180Acetone용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a5cc48d9192b4f709bbe035a2152e27b
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06531470B1

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