Acetic Anhydride → Benzyl (1-cyano-3-phenylpropyl)carbamate

HRID 278038Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 278038
[C:1]([CH:4]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=O)[NH2:2].Cl.N[C@H](C(N)=O)CCC1C=CC=CC=1.C(N1C(=O)CCC1=O)(OCC1C=CC=CC=1)=O.C(OC(=O)C)(=O)C>N1C=CC=CC=1>[C:1]([CH:4]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)#[N:2]

Komponenten

6

Edukt 4

HCID 7918Acetic AnhydrideHCID 3826287Benzyl 2,5-dioxopyrrolidine-1-carboxylateHCID 18685852L-homophenylalaninamide hydrochlorideHCID 76533771Benzyl (1-carbamoyl-3-phenylpropyl)carbamate

Produkt 1

HCID 15946346Benzyl (1-cyano-3-phenylpropyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

2.78 g of benzyl (1-carbamoyl-3-phenylpropyl)carbamate, prepared from L-homophenylalanine amide hydrochloride and N-Cbz-succinimide, were dissolved in 30 ml of dry pyridine and treated with 6 ml of acetic anhydride. The reaction mixture was stirred at 75° C. for 24 h. The cooled solution was concentrated in vacuo, treated with 100 ml of ethyl acetate, and then extracted three times by shaking with 50 ml each of 5% strength citric acid solution and saturated sodium chloride solution. The organic extract was dried over magnesium sulfate, filtered, concentrated in vacuo, and chromatographed on silica gel using n-heptane/ethyl acetate (1/1). Benzyl (1-cyano-3-phenylpropyl)carbamate was obtained, which was employed in the next stage without further purification.

Aufarbeitung

  1. concentrationThe cooled solution was concentrated in vacuo
  2. additiontreated with 100 ml of ethyl acetate
  3. extractionextracted three times
  4. stirringby shaking with 50 ml each of 5% strength citric acid solution and saturated sodium chloride solution
  5. extractionThe organic extract
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customchromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-bcd7af2279944b34bd8f897fe6c1606b
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06358978B1

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