Ethyl acetate hexane → (4R)-3-[(2S)-2-azido-3-butylheptanoyl]-4-benzyl-1,3-oxazolidin-2-one

HRID 1176131Notes

Reaction equation

HRID 1176131 reaction equation
[N-:1]=[N+:2]=[N-:3].CN(C)C(=N)N(C)C.[CH2:12]([C@@H:19]1[CH2:23][O:22][C:21](=[O:24])[N:20]1[C:25](=[O:37])[C@H:26](Br)[CH:27]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH2:30][CH3:31])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCOC(C)=O.CCCCCC>C(#N)C>[N:1]([C@@H:26]([CH:27]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH2:30][CH3:31])[C:25]([N:20]1[C@H:19]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:23][O:22][C:21]1=[O:24])=[O:37])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 66929892(4R)-4-benzyl-3-[(2R)-2-bromo-3-butylheptanoyl]-1,3-oxazolidin-2-oneHCID 131724047Tetramethylguanidine azide

Product 1

HCID 86586539(4R)-3-[(2S)-2-azido-3-butylheptanoyl]-4-benzyl-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Tetramethylguanidine azide (TMGA) (5.398 g, 37.70 mmol) was added dropwise (5 min) to a 25° C. solution of (4R)-4-benzyl-3-[(2R)-2-bromo-3-butylheptanoyl]-1,3-oxazolidin-2-one (4.0 g, 9.42 mmol) in acetonitrile (50 mL). The reaction was stirred for 4 days. An aliquot was taken and TLC (1:4 EtOAc-hexane) indicated that reaction was complete. The solvent was removed in vacuo. The resulting black semi-solid was dissolved in CH2Cl2 (200 mL) and quenched with 1N HCl (30 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to obtain (4R)-3-[(2S)-2-azido-3-butylheptanoyl]-4-benzyl-1,3-oxazolidin-2-one as a crude yellow oil (3.61 g, 99.1%). Mass Spectrum (−ESI): 385 (M−H)−.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe resulting black semi-solid was dissolved in CH2Cl2 (200 mL)
  3. customquenched with 1N HCl (30 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-10e18fb37145451cb51a657669340243
Source dataset
uspto-grants-2010_11
Patent number
US07842718B2

Reaction notes

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