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

HRID 248739
Notes
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Reaction equation

HRID 248739 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:16](O)=[O:17])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[C:4]([C:21]([F:24])([F:23])[F:22])[CH:3]=1.Cl.[CH2:26]([O:28][C:29](=[O:33])[CH2:30][CH2:31][NH2:32])[CH3:27].O.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>>[CH2:26]([O:28][C:29](=[O:33])[CH2:30][CH2:31][NH:32][C:16](=[O:17])[C:15]1[CH:14]=[CH:13][C:12]([S:9](=[O:11])(=[O:10])[NH:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[C:21]([F:22])([F:23])[F:24])=[CH:20][CH:19]=1)[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 150576074-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]benzoic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 53919358
3-[4-[N-(4-Fluoro-2-trifluoromethylphenyl)sulfamoyl]benzoylamino]propionic Acid Ethyl Ester

Procedure

Under the conditions of Example 2(a), 3.633 g (10 mmol) of 4-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]benzoic acid, 1.536 g (10 mmol) of β-alanine 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 and the title compound eluted with ethyl acetate.

Workup

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

Sources & evidence

ORD record
ord-6fbd435f8c6a472a9ac93343b33b35ca
Source dataset
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05210290

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes