Triphenylphosphine → Methyl (2S)-2-benzyloxycarbonylamino-4-cyanobutyrate

HRID 1289244

Reaktionsgleichung

Reaktionsgleichung von HRID 1289244
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:16][CH2:17][C:18](=O)[NH2:19])[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C(Cl)(Cl)(Cl)Cl>[CH2:9]([O:8][C:6]([NH:5][C@@H:4]([CH2:16][CH2:17][C:18]#[N:19])[C:3]([O:2][CH3:1])=[O:21])=[O:7])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

5

Edukt 2

HCID 11776TriphenylphosphineHCID 7020255Z-Gln-ome

Produkt 1

HCID 11000307Methyl (2S)-2-benzyloxycarbonylamino-4-cyanobutyrate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5943Carbon TetrachlorideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of N-benzyloxycarbonyl-L-glutamine methyl ester (25 g) in THF (500 ml) was added dropwise to a stirred solution of triphenylphosphine (44.5 g) in carbon tetrachloride (1 L). The mixture was heated to 50° C. for 2 hours. The mixture was evaporated. The resultant oil was triturated in ethyl acetate. The mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatogaphy using a 1:1 mixture of hexane and ethyl acetate as eluant. There was thus obtained methyl (2S)-2-benzyloxycarbonylarnino-4-cyanobutyrate (19.38 g, 83%).

Aufarbeitung

  1. customThe mixture was evaporated
  2. customThe resultant oil was triturated in ethyl acetate
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated
  5. customThe residue was purified by column chromatogaphy
  6. additiona 1:1 mixture of hexane and ethyl acetate as eluant

Quellen und Nachweise

ORD-Eintrag
ord-ebe61e5660a14d72aaeb847aa9d66948
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05747499

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