Triethylamine → 3-[3-[N-(4-Fluoro-2-trifluoromethylphenyl)sulfamoyl]propionylamino]-3-methoxycarbonylpropionic Acid Methyl Ester

HRID 248744Notes

Reaction equation

HRID 248744 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH2:12][CH2:13][C:14]([OH:16])=O)(=[O:11])=[O:10])=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1.Cl.[CH3:22][O:23][C:24](=[O:32])[C@H:25]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[NH2:26].O.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>>[CH3:31][O:30][C:28](=[O:29])[CH2:27][CH:25]([NH:26][C:14](=[O:16])[CH2:13][CH2:12][S:9](=[O:10])(=[O:11])[NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[C:17]([F:20])([F:19])[F:18])[C:24]([O:23][CH3:22])=[O:32]

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2734892L-Aspartic acid, 1,4-dimethyl ester, hydrochloride (1:1)HCID 104033993-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]propionic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 545598523-[3-[N-(4-Fluoro-2-trifluoromethylphenyl)sulfamoyl]propionylamino]-3-methoxycarbonylpropionic Acid Methyl Ester

Procedure

Under the conditions of Example 2(a), 3.152 g (10 mmol) of 3-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]propionic acid, 1.836 g (10 mmol) of L-aspartic acid dimethyl ester hydrochloride, 1.531 g (10 mmol) of hydroxybenzotriazole, hydrate, as well as 1.012 g (10 mmol) of triethylamine and 2.063 g (10 mmol) of dicyclohexylcarbodiimide are reacted and worked up analogously. The crude product is purified by column chromatography on silica gel. The title compound is eluted with ethyl acetate.

Workup

  1. customThe crude product is purified by column chromatography on silica gel
  2. washThe title compound is eluted with ethyl acetate

Sources & evidence

ORD record
ord-bcd772cb68934cb8b73f453f830fbd64
Source dataset
uspto-grants-1993_05
Patent number
US05210290

Reaction notes

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