Sodium Azide → 4-Benzyl-1,3-oxazolidin-2-one

HRID 2122025Notes

Reaction equation

HRID 2122025 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1C(=O)[C@@H](Br)[C@H](O)COCC1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-]=[N+]=[N-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([CH:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 69881120HCID 69881120, compound

Product 1

HCID 5596684-Benzyl-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
35 °C

Procedure

4(S)-3-[(2R, 3S)-2-Azido-4-benzyloxy-3-hydroxy-butyryl]-4-benzyl-oxazolidin-2-one. To a solution of 4(S)-benzyl-3-[(2S, 3R)-4-benzyloxy-2-bromo-3-hydroxy-butyryl]-oxazolidin-2-one (969 mg, 2.16 mmol) in dimethylformamide (9.0 mL) is added sodium azide (211 mg, 3.25 mmol) and the reaction mixture is stirred at 35° C. for 4 hr. The mixture is diluted with ethyl acetate and washed several times with water, brine and dried over Na2SO4. Filtration and removal of solvents under vacuo gives 4(S)-3-[(2R, 3R)-2-azido-4-benzyloxy-3-hydroxy-butyryl)]-4-benzyl-oxazolidin-2-one as an oil.

Workup

  1. washwashed several times with water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and removal of solvents under vacuo

Sources & evidence

ORD record
ord-f902cabbdbc3430bbeea89a84a8f88a7
Source dataset
uspto-grants-2004_02
Patent number
US06696456B1

Reaction notes

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