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

HRID 248726

Reaction equation

HRID 248726 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:30])[C@H:25]([C@@H:27]([CH3:29])[OH:28])[NH2:26])[CH3:22].O.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>>[CH2:21]([O:23][C:24](=[O:30])[CH: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)[CH:27]([OH:28])[CH3:29])[CH3:22]

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2763096Ethyl L-threoninate hydrochlorideHCID 197640082-[N-(4-fluoro-3-trifluoromethylphenyl)sulfamoyl]acetic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 156765772-[2-[N-(4-Fluoro-3-trifluoromethylphenyl)sulfamoyl]acetylamino]-2-(1-hydroxyethyl)acetic Acid Ethyl Ester

Procedure

Under the conditions of Example 2(a), 3.012 g (10 mmol) of 2-[N-(4-fluoro-3-trifluoromethylphenyl)sulfamoyl]acetic acid, 1.736 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-eb41d05580b34965a643d6950037abb8
Source dataset
uspto-grants-1993_05
Patent number
US05210290

Linked notes

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