Water → HCID 10473077, compound

HRID 1823049Notes

Reaction equation

HRID 1823049 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)[CH2:6]1)=O.[CH3:27][NH2:28].O>C(O)C>[CH3:27][NH:28][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)[CH2:6]1)=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 68614487HCID 68614487, compound

Product 1

HCID 10473077HCID 10473077, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 400 mg (1.1 mmol) of (RS)-(E)-1-{4-[2-(4-methoxy-phenyl)-vinyl]-phenyl}-5-oxo-pyrrolidine-3-carboxylic acid methyl ester in 1.4 ml of a solution of methylamine in ethanol (33%) is heated at 90° C. for 18 h in a sealed vial. For the working-up, the cooled solution is treated with water to precipitate the product. The solid material is collected on a filter funnel, washed with water, finally, with heptane. After crystallization of the crude amide from a mixture of N,N-dimethylformamide and methanol, 98 mg (25% of theory) of (RS)-(E)-1-{4-[2-(4-methoxy-phenyl)-vinyl]-phenyl}-5-oxo-pyrrolidine-3-carboxylic acid methylamide are obtained as a light brown solid; MS: m/e=351 (M+H)+.

Workup

  1. customto precipitate the product
  2. customThe solid material is collected on a filter funnel
  3. washwashed with water
  4. customAfter crystallization of the crude amide
  5. additionfrom a mixture of N,N-dimethylformamide and methanol, 98 mg (25% of theory) of (RS)-(E)-1-{4-[2-(4-methoxy-phenyl)-vinyl]-phenyl}-5-oxo-pyrrolidine-3-carboxylic acid methylamide
  6. customare obtained as a light brown solid

Sources & evidence

ORD record
ord-82c347aa43e64ae58f95eaffc0ba8b60
Source dataset
uspto-grants-2006_05
Patent number
US07037935B2

Reaction notes

Loading…