Triethylamine → 2-[3-[N-(4-Fluoro-2-trifluoromethylphenyl)sulfamoyl]propionylamino]-2-(1-hydroxyethyl)acetic Acid Ethyl Ester

HRID 248743Notes

Reaction equation

HRID 248743 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.[CH2:22]([O:24][C:25](=[O:31])[C@H:26]([C@@H:28]([CH3:30])[OH:29])[NH2:27])[CH3:23].O.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>>[CH2:22]([O:24][C:25](=[O:31])[CH:26]([NH:27][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])[CH:28]([OH:29])[CH3:30])[CH3:23]

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2763096Ethyl L-threoninate hydrochlorideHCID 104033993-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]propionic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 544883442-[3-[N-(4-Fluoro-2-trifluoromethylphenyl)sulfamoyl]propionylamino]-2-(1-hydroxyethyl)acetic Acid Ethyl Ester

Procedure

Under the conditions of Example 2(a), 3.152 g (10 mmol) of 3-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]propionic acid, 1.736 g (10 mmol) of L-threonine ethyl 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-5f3867f8ba7e4ffeb7e359e728284923
Source dataset
uspto-grants-1993_05
Patent number
US05210290

Reaction notes

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