N-methyl-2-pyrrolidone → 3-Hydroxy-alpha-methyl-L-tyrosine 1-(2,2-dimethyl-1-oxopropoxy)ethyl ester

HRID 1906986

Reaktionsgleichung

Reaktionsgleichung von HRID 1906986
[CH3:1][C@@:2]([NH2:15])([C:12]([OH:14])=[O:13])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:11])=[C:8]([OH:10])[CH:9]=1.[Br-].[Li+].CN1CCCC1=O.[C:25]([O:31][CH:32](Cl)[CH3:33])(=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27]>C(OCC)(=O)C>[OH:10][C:8]1[CH:9]=[C:4]([CH2:3][C@@:2]([CH3:1])([C:12]([O:14][CH:32]([O:31][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])[CH3:33])=[O:13])[NH2:15])[CH:5]=[CH:6][C:7]=1[OH:11]

Komponenten

6

Edukt 4

HCID 13387N-methyl-2-pyrrolidoneHCID 38853MethyldopaHCID 82050Lithium BromideHCID 30161741-Chloroethyl pivalate

Produkt 1

HCID 881263-Hydroxy-alpha-methyl-L-tyrosine 1-(2,2-dimethyl-1-oxopropoxy)ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

10 grams (0.047 mole) of α-methyldopa, 4.7 grams of powdered 4A molecular sieves, 6.1 grams (0.070 mole) of lithium bromide and 47 milliliters of N-methylpyrrolidinone were stirred for about one hour at 25° C. To this mixture, 8.1 grams (0.049 mole) of α-chloroethyl pivalate was added and the mixture was aged at 55° C. for 8 hours. At the end of this time, the mixture was cooled to 25° C., diluted with 100 milliliters of ethyl acetate and washed successively with one 200 milliliter and two 100 milliliter portions of saturated sodium bicarbonate solution. The combined sodium bicarbonate washes were extracted with two 100 milliliter portions of ethyl acetate and the combined ethyl acetate extracts concentrated under vacuum to 150 milliliters. The assay yield of α-pivaloyloxyethyl (S)-3-(3,4-dihydroxyphenyl)-2-methylalaninate was found to be 14.4 grams or 90 percent of theoretical.

Aufarbeitung

  1. waitthe mixture was aged at 55° C. for 8 hours
  2. temperatureAt the end of this time, the mixture was cooled to 25° C.
  3. washwashed successively with one 200 milliliter and two 100 milliliter portions of saturated sodium bicarbonate solution
  4. extractionThe combined sodium bicarbonate washes were extracted with two 100 milliliter portions of ethyl acetate
  5. concentrationthe combined ethyl acetate extracts concentrated under vacuum to 150 milliliters

Quellen und Nachweise

ORD-Eintrag
ord-e6e58058f4af4af3a05bd51fad74b2f4
Quelldatensatz
uspto-grants-1987_03
Patentnummer
US04654433

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