1,2-Dichloroethane → HCID 59375055, compound

HRID 1811069Notes

Reaction equation

HRID 1811069 reaction equation
[Br:1][C:2]1[C:3]([CH3:17])=[C:4]([N:8]2[C:12](=[O:13])[CH2:11][CH:10]([C:14](O)=[O:15])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(Cl)CCl.C1C=CC2N(O)N=[N:28]C=2C=1.N>C1COCC1.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([CH3:17])=[C:4]([N:8]2[C:12](=[O:13])[CH2:11][CH:10]([C:14]([NH2:28])=[O:15])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 66605974HCID 66605974, compound2×

Product 1

HCID 59375055HCID 59375055, compoundYield 26.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(3-bromo-2-methylphenyl)-5-oxopyrrolidine-3-carboxylic acid (Intermediate 41-10, 100 mg, 0.335 mmol), EDC (129 mg, 0.671 mmol), HOBT (103 mg, 0.671 mmol) and 28% aqueous ammonia in THF (2 mL) was stirred at rt for 5 h. The mixture was diluted with ethyl acetate, washed with NaHCO3 (aq) and water, and dried and concentrated. The residue was purified by column chromatography (eluting with 90:10 DCM-methanol) to provide 1-(3-bromo-2-methylphenyl)-5-oxopyrrolidine-3-carboxamide as a white solid (26 mg, 26%). Mass spectrum m/z 297, 299 (M+H)+.

Workup

  1. washwashed with NaHCO3 (aq) and water
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (eluting with 90:10 DCM-methanol)

Sources & evidence

ORD record
ord-56a525a753354e98a32a5485d6d01f00
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

Loading…