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

HRID 248714

Reaction equation

HRID 248714 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])=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:3]=1.Cl.[CH3:21][O:22][C:23](=[O:28])[C@H:24]([CH2:26][OH:27])[NH2:25].O.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>>[CH3:21][O:22][C:23](=[O:28])[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])=[CH:3][C:4]=1[C:16]([F:19])([F:18])[F:17])[CH2:26][OH:27]

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 156765552-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]acetic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 156765582-[2-[N-(4-Fluoro-2-trifluoromethylphenyl)sulfamoyl]acetylamino]-2-hydroxymethylacetic Acid Methyl Ester

Procedure

Under the conditions of Example 2(a), 3.29 g (10.93 mmol) of 2-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]acetic acid, 1.70 g (10.93 mmol) L-serine methyl ester hydrochloride, 1.67 g (10.93 mmol) of hydroxybenzotriazole, hydrate, as well as 1.11 g (10.93 mmol) of triethylamine and 2.26 g (10.93 mmol) of dicyclohexylcarbodiimide are reacted and worked up analogously. The crude product is chromatographed on silica gel. The title compound is eluted with ethanol and crystallized upon concentration.

Workup

  1. customThe crude product is chromatographed on silica gel
  2. washThe title compound is eluted with ethanol
  3. customcrystallized upon concentration

Sources & evidence

ORD record
ord-9e464e8c790a4afc8007593b85eaa8fa
Source dataset
uspto-grants-1993_05
Patent number
US05210290

Linked notes

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