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

反応式

HRID 744808 の反応式
[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]

参加物

5

反応物 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

生成物 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)-

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4aaff9d4bd674caba17f861fcc7c0366
出典データセット
uspto-grants-1996_09
特許番号
US05559111

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