Triethylamine → 2-Benzyl-2-formamidoacetic acid methyl ester

HRID 1821633

Reaktionsgleichung

Reaktionsgleichung von HRID 1821633
[CH:1](OCC#N)=[O:2].Cl.[CH3:8][O:9][C:10](=[O:20])[C@H:11]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH2:12].C(N(CC)CC)C>ClCCl>[CH:1]([NH:12][CH:11]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([O:9][CH3:8])=[O:20])=[O:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 4205685(Formyloxy)acetonitrile

Produkt 1

HCID 5955292-Benzyl-2-formamidoacetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Cyanomethyl formate (Aldrich, Order No. 453579, 5.05 g, 59.3 mmole) was suspended together with the phenylalanine methyl ester hydrochloride (Aldrich, Order No. 525472, 12.80 g, 59.3 mmole) in 80 ml dichloromethane and cooled to 0° C. in an ice bath. Triethylamine (6.01 g, 59.3 mmole) dissolved in 15 ml of dichloromethane was then added and the mixture was stirred for 16 hours at room temperature. A clear solution formed. In order to work up the mixture the latter was diluted with 100 ml of dichloromethane and washed firstly with 200 ml of saturated NaHCO3 solution and then twice with saturated NaCl solution. The organic phase was dried over magnesium sulfate and concentrated by evaporation. The product obtained was used without further purification for the next stage.

Aufarbeitung

  1. additionwas then added
  2. customA clear solution formed
  3. washwashed firstly with 200 ml of saturated NaHCO3 solution
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe product obtained
  7. customwas used without further purification for the next stage

Quellen und Nachweise

ORD-Eintrag
ord-f55b2bd79a4941678b2e99a6a610d7b7
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608619B2

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