4-Nitrobenzenesulfonyl chloride → (s)-(4-Nitro-benzenesulfonylamino)-phenyl-acetic acid

HRID 2360624

Reaktionsgleichung

Reaktionsgleichung von HRID 2360624
[CH:1]1[CH:6]=[CH:5][C:4]([C@H:7]([NH2:11])[C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.C(N(CC)CC)C.[N+:19]([C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1)([O-:21])=[O:20]>O.O1CCOCC1>[N+:19]([C:22]1[CH:23]=[CH:24][C:25]([S:28]([NH:11][C@@H:7]([C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)[C:8]([OH:10])=[O:9])(=[O:30])=[O:29])=[CH:26][CH:27]=1)([O-:21])=[O:20]

Komponenten

6

Edukt 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 99291L-Phenylglycine

Produkt 1

HCID 362697(s)-(4-Nitro-benzenesulfonylamino)-phenyl-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

To a solution of L-phenylglycine (0.227 g, 1.5 mmol) in water (5 ml) and dioxane (5 ml) was added triethylamine (0.42 ml, 3.0 mmol) followed by slow addition of 4-nitrobenzene sulphonyl chloride (0.5 g, 2.3 mmol) in dioxane (5 ml) at 0° C. After stirring for 45 minutes the reaction mixture was evaporated to dryness, re-dissolved in EtOAc and washed with saturated NaHCO3 solution (2×20 ml) and water (10 ml). The EtOAc layer was dried over Na2SO4, filtered and evaporated to dryness. LCMS purity 75%, (molecular ion not observed) yield 0.58 g, (76%). This material was used without any purification.

Aufarbeitung

  1. customwas evaporated to dryness
  2. dissolutionre-dissolved in EtOAc
  3. washwashed with saturated NaHCO3 solution (2×20 ml) and water (10 ml)
  4. dry with materialThe EtOAc layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThis material was used without any purification

Quellen und Nachweise

ORD-Eintrag
ord-6c004a69f7414a599c20f987058de583
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08686032B2

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