Triethylamine → 2,6-Bis-(2-benzyloxy-acetylamino)-hexanoic acid methyl ester

HRID 406791

Reaktionsgleichung

Reaktionsgleichung von HRID 406791
Cl.Cl.[CH3:3][O:4][C:5](=[O:13])[C@H:6]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])[NH2:7].C(N([CH2:19][CH3:20])CC)C.[CH2:21]([O:28][CH2:29][C:30](Cl)=[O:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(OCC)(=O)C>[CH3:3][O:4][C:5](=[O:13])[CH:6]([NH:7][C:30](=[O:31])[CH2:29][O:28][CH2:21][C:20]1[CH:19]=[CH:24][CH:23]=[CH:22][CH:27]=1)[CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:30](=[O:31])[CH2:29][O:28][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 117778Methyl L-lysinate dihydrochlorideHCID 177085Benzyloxyacetyl chloride

Produkt 1

HCID 596824872,6-Bis-(2-benzyloxy-acetylamino)-hexanoic acid methyl esterAusbeute 31,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of L-lysine methyl ester dihydrochloride (50 grams, 214.4 mmol), triethylamine (131 grams, 1.294 moles) in ethyl acetate (750 mL) at room temperature was added benzyloxy acetyl chloride (120 grams, 650.4 mmol) drop wise. The mixture was further stirred at room temperature for 2 hours. The solids were filtered off. The organic phase was washed with 5% sodium bicarbonate (2×100 mL), water (2×100 mL), dried over sodium sulphate and distilled. The crude 2 was purified by column chromatography on silica gel using Benzene:Ethyl acetate (9:1) to get pure 2 (30 grams, 31.8%) as a white powder.

Aufarbeitung

  1. filtrationThe solids were filtered off
  2. washThe organic phase was washed with 5% sodium bicarbonate (2×100 mL), water (2×100 mL)
  3. dry with materialdried over sodium sulphate
  4. distillationdistilled
  5. customThe crude 2 was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-5e094245c1254f09b39405a0d1cdd61d
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754135B2

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