Hydrochloric Acid → 2-Amino-3-(4-fluoro-phenylamino)-2-methyl-propionic acid methyl ester

HRID 2426997Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2426997
[CH3:1][O:2][C:3](=[O:23])[C:4]([NH:15]C(OC(C)(C)C)=O)([CH3:14])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.Cl.[OH-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:23])[C:4]([NH2:15])([CH3:14])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 576789232-tert-Butoxycarbonylamino-3-(4-fluoro-phenylamino)-2-methyl-propionic acid methyl ester

Produkt 1

HCID 576789242-Amino-3-(4-fluoro-phenylamino)-2-methyl-propionic acid methyl esterAusbeute 46,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a solution of 2-tert-butoxycarbonylamino-3-(4-fluoro-phenylamino)-2-methyl-propionic acid methyl ester (954 mg, 2.92 mmol) in methanol (10 mL) was added HCl (3 mL, 12 N). The mixture was heated to 55° C. until the MS indicated no starting material remained. After cooling to ambient temperature, the solution was treated with aqueous NaOH (40 mL, 1N) and extracted several times with DCM. The combined extracts were concentrated and purified by flash chromatography (SiO2, 5% MeOH/DCM) to yield the title compound as a yellow oil (305 mg, 46%).

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted several times with DCM
  3. concentrationThe combined extracts were concentrated
  4. custompurified by flash chromatography (SiO2, 5% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-864395abe5ec489994916f226b692b8d
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968580B2

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