Triethylamine → 2-[2-[N-(4-Fluoro-3-trifluoromethylphenyl)sulfamoyl]-acetylamino]acetic Acid Ethyl Ester

HRID 248713Notes

Reaction equation

HRID 248713 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH2:12][C:13]([OH:15])=O)(=[O:11])=[O:10])=[CH:4][C:3]=1[C:16]([F:19])([F:18])[F:17].Cl.[CH2:21]([O:23][C:24](=[O:27])[CH2:25][NH2:26])[CH3:22].O.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH2:21]([O:23][C:24](=[O:27])[CH2:25][NH:26][C:13](=[O:15])[CH2:12][S:9](=[O:10])(=[O:11])[NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:16]([F:19])([F:18])[F:17])[CH:4]=1)[CH3:22]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2723640Glycine ethyl ester, hydrochlorideHCID 197640082-[N-(4-fluoro-3-trifluoromethylphenyl)sulfamoyl]acetic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 156765572-[2-[N-(4-Fluoro-3-trifluoromethylphenyl)sulfamoyl]-acetylamino]acetic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

Under nitrogen, 1.81 g (6 mmol) of 2-[2-[N-(4-fluoro-3-trifluoromethylphenyl)sulfamoyl]acetic acid, 0.845 g (6 mmol) of glycine ethyl ester hydrochloride (98%), and 0.919 g (6 mmol) of hydroxybenzotriazole, hydrate, are added to 100 ml of dimethylformamide and the mixture is cooled to -10° C. under agitation. Then 0.607 g (6 mmol) of triethylamine is added thereto, the mixture is agitated for 10 minutes and combined with 1.24 g (6 mmol) of dicyclohexylcarbodiimide. The mixture is stirred for another hour at the low temperature and then overnight without cooling. The mixture is suctioned off from the solid matter, the solution is concentrated to dryness under vacuum, and the residue is distributed between sodium bicarbonate solution and ethyl acetate. The ethyl acetate solution is washed with water, dried over sodium sulfate, and concentrated to dryness under vacuum. The residue is crystallized from ethyl acetate/hexane, thus obtaining 1.72 g (74.1% of theory) of the title compound.

Workup

  1. stirringThe mixture is stirred for another hour at the low temperature
  2. temperatureovernight without cooling
  3. concentrationthe solution is concentrated to dryness under vacuum
  4. washThe ethyl acetate solution is washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness under vacuum
  7. customThe residue is crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-8aa71a47b68641a79a3ac204511d370e
Source dataset
uspto-grants-1993_05
Patent number
US05210290

Reaction notes

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