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 264920

Reaction equation

HRID 264920 reaction equation
[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]

Participants

5

Reactant 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

Product 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)-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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)-benzyloxazolidin-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.

Workup

  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

Sources & evidence

ORD record
ord-da101d96fc9f4b119aff6251a69e25f2
Source dataset
uspto-grants-1997_07
Patent number
US05646143

Linked notes

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