Azide → 2-Oxazolidinone, 3-[(2S,4S)-4-azido-2-(1-methylethyl)-1-oxo-4-[(2S,4S)-tetrahydro-4-(1-methylethyl)-5-oxo-2-furanyl]butyl]-4-(phenylmethyl)-, (4S)-

HRID 744808

반응식

HRID 744808 반응식
[N-:1]=[N+:2]=[N-:3].C([N+](CCCC)(CCCC)CCCC)CCC.[CH:21]([C@@H:24]1[CH2:28][C@@H:27]([C@H:29](Br)[CH2:30][C@H:31]([C:35]([N:37]2[C@@H:41]([CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH2:40][O:39][C:38]2=[O:49])=[O:36])[CH:32]([CH3:34])[CH3:33])[O:26][C:25]1=[O:51])([CH3:23])[CH3:22].[N-]=[N+]=[N-]>C1(C)C=CC=CC=1>[CH:21]([C@@H:24]1[CH2:28][C@@H:27]([C@@H:29]([N:1]=[N+:2]=[N-:3])[CH2:30][C@H:31]([C:35]([N:37]2[C@@H:41]([CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH2:40][O:39][C:38]2=[O:49])=[O:36])[CH:32]([CH3:34])[CH3:33])[O:26][C:25]1=[O:51])([CH3:22])[CH3:23]

참가 물질

5

반응물 3

HCID 33558AzideHCID 57432321-Butanaminium, N,N,N-tributyl-, azideHCID 54147056(4S)-3-[(2S,4R)-4-Bromo-2-(1-methylethyl)-1-oxo-4-[(2S,4S)-tetrahydro-4-(1-methylethyl)-5-oxo-2-furanyl]butyl]-4-(phenylmethyl)-2-oxazolidinone

생성물 1

HCID 533855072-Oxazolidinone, 3-[(2S,4S)-4-azido-2-(1-methylethyl)-1-oxo-4-[(2S,4S)-tetrahydro-4-(1-methylethyl)-5-oxo-2-furanyl]butyl]-4-(phenylmethyl)-, (4S)-

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

13.6 g of freshly dried tetrabutylammonium azide are added to a solution, stirred at room temperature, of 17.8 g of 3(S)-isopropyl-5(S)-{1(R)-bromo-4-methyl-3(S)-[(4(S)-benzyl-oxazolidin-2-on-3-yl)-carbonyl]-pentyl}-tetrahydrofuran-2-one in 180 ml of toluene, and a further 10 g of the azide are added in the course of 160 hours' stirring at room temperature. The reaction mixture is then partitioned between ethyl acetate and water (2x) and saturated sodium chloride solution (1x). The organic phases are combined, dried over sodium sulfate and concentrated. The title compound is obtained from the evaporation residue by means of FC (hexane/ethyl acetate=8:2) and crystallisation from diethyl ether/hexane: m.p.=102°-103° C.; Rf (hexane/ethyl acetate=8:2)=0.2; HPLC Rt =18.55 minutes; FAB-MS (M+H)+ =457.

후처리

  1. customThe reaction mixture is then partitioned between ethyl acetate and water (2x) and saturated sodium chloride solution (1x)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4aaff9d4bd674caba17f861fcc7c0366
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05559111

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