Triethylamine → 1-(4-Fluoro-phenyl)-4-methyl-2-oxo-imidazolidine-4-carboxylic acid methyl ester

HRID 491763Notes

Reaction equation

HRID 491763 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]([NH2:15])([CH3:14])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.C(N(CC)CC)C.Cl[C:25](Cl)([O:27]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1.C(Cl)Cl>[CH3:1][O:2][C:3]([C:4]1([CH3:14])[CH2:5][N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[C:25](=[O:27])[NH:15]1)=[O:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 576789242-Amino-3-(4-fluoro-phenylamino)-2-methyl-propionic acid methyl ester

Product 1

HCID 441926211-(4-Fluoro-phenyl)-4-methyl-2-oxo-imidazolidine-4-carboxylic acid methyl esterYield 145.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-amino-3-(4-fluoro-phenylamino)-2-methyl-propionic acid methyl ester (282 mg, 1.25 mmol) in THF (10 mL) was treated with triethylamine (2.00 mL, 14.3 mmol) and cooled to 0° C. under argon. A solution of triphosgene (211 mg, 0.71 mmol) was added to the reaction dropwise and the mixture allowed to reach room temperature. After 1 hour, the mixture was diluted with DCM, washed with 1N HCl and the organic layers concentrated in vacuo. The resulting residue was purified by flash chromatography to afford the product (260 mg, 82%).

Workup

  1. customto reach room temperature
  2. washwashed with 1N HCl
  3. concentrationthe organic layers concentrated in vacuo
  4. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-a309255ca64f41c58aab7c4287d5e939
Source dataset
uspto-grants-2009_05
Patent number
US07531565B2

Reaction notes

Loading…