Triethylamine → N-6-bromohexanoyl-L-leucine ethyl ester

HRID 864465Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 864465
Cl.[CH2:2]([O:4][C:5](=[O:12])[C@H:6]([CH2:8][CH:9]([CH3:11])[CH3:10])[NH2:7])[CH3:3].C(N(CC)CC)C.[Br:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26](Cl)=[O:27]>C1COCC1.[Cl-].[NH4+].C(OCC)(=O)C>[CH2:2]([O:4][C:5](=[O:12])[C@H:6]([CH2:8][CH:9]([CH3:11])[CH3:10])[NH:7][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][Br:20])[CH3:3]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 898486-Bromohexanoyl chlorideHCID 11658447L-Leucine, ethyl ester, hydrochloride (1:1)

Produkt 1

HCID 22866411N-6-bromohexanoyl-L-leucine ethyl esterAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

A stirred suspension of L-leucine ethyl ester hydrochloride (8.38 g, 45 mmol) in dry THF (80 ml) at room temperature was treated with triethylamine (6.3 ml, 45 mmol). The reaction mixture was treated with 6-bromohexanoyl chloride (6.91 ml, 45 mmol). The reaction mixture was stirred for 4 h at room temperature and then diluted with a mixture of saturated aqueous ammonium chloride and ethyl acetate. The organic layer was separated, washed with saturated aqueous ammonium chloride, dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to give N-6-bromohexanoyl-L-leucine ethyl ester (12.1 g, 80%) as an oil which was used for the next step without further purification.

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous ammonium chloride
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-825b0c937ac6420892ded97bbd91ba54
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05563151

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