Hydrochloric Acid → 2-(3,4-Dichloro-phenylamino)-propionic Acid

HRID 1096190Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1096190
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([Cl:9])[CH:3]=1.[NH2:10][C@H:11]([C:13]([OH:15])=[O:14])[CH3:12].CN(C)CCO.Cl>O>[Cl:9][C:4]1[CH:3]=[C:2]([NH:10][CH:11]([CH3:12])[C:13]([OH:15])=[O:14])[CH:7]=[CH:6][C:5]=1[Cl:8]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 5950L-AlanineHCID 79022-(Dimethylamino)ethanolHCID 290134-Bromo-1,2-dichlorobenzene

Produkt 1

HCID 69164262-(3,4-Dichloro-phenylamino)-propionic AcidAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 1-bromo-3,4-dichlorobenzene (5.10 g, 22.1 mmol), L-alanine (2.96 g, 33.2 mmol) copper(I) iodide (421 mg, 2.21 mmol), tri-potassium phosphate n-hydrate (15.3 g, 66.4 mmol), 2-(dimethylamino)ethanol (5.92 g, 66.4 mmol), and water (22 mL) was heated at 90° C. for 40 h, then poured onto ice water. The pH was set to 6 with 25% aq. HCl solution, and the mixture was extracted with EtOAc. The aqueous phase was acidified to pH 4.5 and extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; EtOAc) afforded the title compound (2.71 g, 53%) as a 60:40 mixture of the (S) and (R) stereoisomers. Light brown solid, MS: 232.1 (M−H)−.

Aufarbeitung

  1. additionpoured onto ice water
  2. extractionthe mixture was extracted with EtOAc
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a5572e7b485c4f0883285722f5f854f1
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138175B2

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