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

HRID 248727Notes

Reaction equation

HRID 248727 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.[CH3:21][O:22][C:23](=[O:31])[C@H:24]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[NH2:25].O.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>>[CH3:30][O:29][C:27](=[O:28])[CH2:26][CH:24]([NH:25][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)[C:23]([O:22][CH3:21])=[O:31]

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2734892L-Aspartic acid, 1,4-dimethyl ester, hydrochloride (1:1)HCID 197640082-[N-(4-fluoro-3-trifluoromethylphenyl)sulfamoyl]acetic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 156765783-[2-[N-(4-Fluoro-3-trifluoromethylphenyl)sulfamoyl]acetylamino]-3-methoxycarbonylpropionic Acid Methyl Ester

Procedure

Under the conditions of Example 2(a), 3.012 g (10 mmol) of 2-[N-(4-fluoro-3-trifluoromethylphenyl)sulfamoyl]acetic 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 chromatographed on silica gel. The title compound is eluted with ethyl acetate.

Workup

  1. customThe crude product is chromatographed on silica gel
  2. washThe title compound is eluted with ethyl acetate

Sources & evidence

ORD record
ord-959443e4a2544ca28c34658ea6fe4ed9
Source dataset
uspto-grants-1993_05
Patent number
US05210290

Reaction notes

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