Pyrrole-2-Carboxylic Acid → HCID 67033510, compound

HRID 539094Notes

Reaction equation

HRID 539094 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1.N1C=CC=C1C(O)=O.[N:22]1([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CS(C)=O.[Cu]I>[O:13]=[C:10]1[NH:9][CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:25]2[CH2:24][CH2:23][N:22]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:27][CH2:26]2)[CH2:12][O:11]1

Participants

7

Reactant 4

HCID 12473Pyrrole-2-Carboxylic AcidHCID 62657Potassium Phosphate, TribasicHCID 143452tert-Butyl piperazine-1-carboxylateHCID 65583853HCID 65583853, compound

Product 1

HCID 67033510HCID 67033510, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(2-bromophenyl)oxazolidin-2-one (497 mg, 2.05 mmol), 1H-pyrrole-2-carboxylic acid (137 mg, 1.23 mmol), tert-butyl piperazine-1-carboxylate (765 mg, 4.11 mmol), copper(I) iodide (117 mg, 0.616 mmol) and K3PO4 (1.74 g, 8.21 mmol) in DMSO (15 mL) was heated at 90° C. for 8 hours. After cooling, the reaction mixture was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by column chromatography (hexane/EtOAc, 1:1) to give tert-butyl 4-(2-(2-oxooxazolidin-4-yl)phenyl)piperazine-1-carboxylate (462 mg, 65%).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (hexane/EtOAc, 1:1)

Sources & evidence

ORD record
ord-c501edf387e14ec9aba9fb97444abd8e
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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