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

HRID 248729

Reaction equation

HRID 248729 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[CH:20]=[CH:19][C:15](C(O)=O)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][C:3]=1[C:21]([F:24])([F:23])[F:22].Cl.[CH2:26]([O:28][C:29](=[O:35])[C@H:30]([C@@H:32]([CH3:34])[OH:33])[NH2:31])[CH3:27].O.[OH:37][C:38]1C2N=NNC=2C=CC=1.C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>>[CH2:26]([O:28][C:29](=[O:35])[CH:30]([NH:31][C:38](=[O:37])[C:13]1[CH:14]=[CH:15][CH:19]=[CH:20][C:12]=1[S:9](=[O:11])(=[O:10])[NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:21]([F:22])([F:24])[F:23])[CH:4]=1)[CH:32]([OH:33])[CH3:34])[CH3:27]

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2763096Ethyl L-threoninate hydrochlorideHCID 36999904-[N-(4-fluoro-3-trifluoromethylphenyl)sulfamoyl)benzoic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 156765822-[2-[N-(4-Fluoro-3-trifluoromethylphenyl)sulfamoyl]benzoylamino]-2-(1-hydroxyethyl)acetic Acid Ethyl Ester

Procedure

Under the conditions of Example 2(a), 3.633 g (10 mmol) of 4-[N-(4-Fluoro-3-trifluoromethylphenyl)sulfamoyl]benzoic 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 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-97698e87395e4adf8687f2c0fbc7cbbd
Source dataset
uspto-grants-1993_05
Patent number
US05210290

Linked notes

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