Sodium Azide → (5R)-5-(Azidomethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one

HRID 2066808

반응식

HRID 2066808 반응식
Cl[CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][N:10]=2)[CH2:4]1.[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C)C=O.O>[N:16]([CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][N:10]=2)[CH2:4]1)=[N+:17]=[N-:18]

참가 물질

5

반응물 2

HCID 33557Sodium AzideHCID 59409863(5R)-5-(chloromethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one2회

생성물 1

HCID 59409901(5R)-5-(Azidomethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one수율 93.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of (5R)-5-(chloromethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one (2.32 g, INTERMEDIATE 7) and sodium azide (1.22 g) was heated to 100° C. in 75 ml of dimethylformamide for 15 h. The mixture was then diluted with 500 ml of water and extracted with 500 ml of ethyl acetate (3×). The combined organic layers were washed with water (250 ml) and brine (250 ml). They were then dried over sodium sulfate and concentrated in vacuo to provide 2.22 g (93%) of the title compound in >95% purity via LC/MS. Mass spectrum (ESI) 254.1 (M+1).

후처리

  1. extractionextracted with 500 ml of ethyl acetate (3×)
  2. washThe combined organic layers were washed with water (250 ml) and brine (250 ml)
  3. dry with materialThey were then dried over sodium sulfate
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-45672aaf143449068956c50a354f27d4
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293721B2

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