Pyrazole → HCID 69364737, compound

HRID 723784Notes

Reaction equation

HRID 723784 reaction equation
[H-].[Na+].[CH3:3][S:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][C@H:14]([CH2:16]OS(C)(=O)=O)[O:13][C:12]2=[O:22])=[CH:7][CH:6]=1.[NH:23]1[CH:27]=[CH:26][CH:25]=[N:24]1>CN(C)C=O.O>[CH3:3][S:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][C@H:14]([CH2:16][N:23]3[CH:27]=[CH:26][CH:25]=[N:24]3)[O:13][C:12]2=[O:22])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 87799035HCID 87799035, compound

Product 1

HCID 69364737HCID 69364737, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

Sodium hydride (80% in oil, 63 mg, 2.1 mM) was stirred under nitrogen in N,N-dimethylformamide (2 ml), (5R)-3-(4-methylthiophenyl)-5-methanesulfonyloxymethyl-oxazolidin-2-one (630 mg, 2 mM) dissolved in N,N-dimethylformamide (10 ml) added, followed by pyrazole (140 mg, 2 mM) dissolved in N,N-dimethylformamide (2 ml). Stirring was continued for 1.5 hours at ambient temperature. After diluting with water (30 ml) and stirring for 1 hour, the precipitate was filtered to give the desired product (190 mg, mp 72–73°).

Workup

  1. additionadded
  2. stirringstirring for 1 hour
  3. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-aa9838d4d5354ca08c3e10e5be1b61de
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

Loading…