Sulfuric Acid → O-Methyl-L-tyrosine methyl ester

HRID 1855650Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1855650
C(OC([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=O)(C)(C)C.S(=O)(=O)(O)O.[OH-].[Na+].[C:29](=O)([O-])O.[Na+]>CO>[NH2:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:10]([O:12][CH3:29])=[O:11]

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 2762280Boc-O-methyl-L-tyrosine

Produkt 1

HCID 10856719O-Methyl-L-tyrosine methyl esterAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To 10 g (33.8 mmol) of (S)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionic acid are added 75 ml of methanol and then 10 ml of sulfuric acid dropwise over 30 minutes. After 30 hours, the reaction medium is basified to pH 8-9 by adding aqueous 10N sodium hydroxide solution followed by saturated sodium hydrogen carbonate solution. The organic products are extracted with dichloromethane. The organic phase is dried over magnesium sulfate and then filtered, and the solvents are evaporated off. 6.36 g of methyl (S)-2-amino-3-(4-methoxyphenyl)propionate in the form of a brown oil are obtained in a yield of 90%.

Aufarbeitung

  1. extractionThe organic products are extracted with dichloromethane
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvents are evaporated off

Quellen und Nachweise

ORD-Eintrag
ord-1c44ed467fe3447493cb59d5169c101c
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962846B2

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