Carbonic acid di-2-pyridyl ester → (S)-5-(3-nitro-pyrazol-1-ylmethyl)-oxazolidin-2-one

HRID 19187Notes

Reaction equation

HRID 19187 reaction equation
[NH2:1][CH2:2][C@H:3]([OH:13])[CH2:4][N:5]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[N:6]1.[C:14](=O)(OC1C=CC=CN=1)[O:15]C1C=CC=CN=1>ClCCl>[N+:10]([C:7]1[CH:8]=[CH:9][N:5]([CH2:4][C@H:3]2[O:13][C:14](=[O:15])[NH:1][CH2:2]2)[N:6]=1)([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 2757370Carbonic acid di-2-pyridyl esterHCID 66900594HCID 66900594, compound

Product 1

HCID 66895029(S)-5-(3-nitro-pyrazol-1-ylmethyl)-oxazolidin-2-oneYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-1-amino-3-(3-nitro-pyrazole-1-yl)-propan-2-ol (0.65 g, 3.49 mmol) in dichloromethane (15 mL) was added di-2-pyridyl carbonate (0.76 g, 3.49 mmol). The reaction mixture was stirred at room temperature for 2 h and then diluted with dichloromethane. The organic layer was washed with a saturated sodium chloride solution and dried over magnesium sulfate. The crude product obtained after concentration, was purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% to 10% methanol/dichloromethane) to afford (S)-5-(3-nitro-pyrazol-1-ylmethyl)-oxazolidin-2-one (0.36 g, 49%) as a clear colorless oil: HR-ES-MS m/z calculated for C7H8N4O4 [M]+ 212, observed 213 [M+H]+.

Workup

  1. washThe organic layer was washed with a saturated sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. customThe crude product obtained
  4. concentrationafter concentration
  5. customwas purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% to 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-1489519eee5840f0a3e31c791628fad8
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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