N-(tert-butoxycarbonyl)glycine → Ethyl 3-(2-{(tert-butoxycarbonyl)amino}acetylamino)propionate

HRID 272060

Reaktionsgleichung

Reaktionsgleichung von HRID 272060
Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:10]([O:14][C:15]([NH:17][CH2:18][C:19](O)=[O:20])=[O:16])([CH3:13])([CH3:12])[CH3:11].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)(Cl)Cl.C(N(CC)CC)C>[C:10]([O:14][C:15]([NH:17][CH2:18][C:19]([NH:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:20])=[O:16])([CH3:13])([CH3:12])[CH3:11]

Komponenten

7

Edukt 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 21893946Ethyl 3-(2-{(tert-butoxycarbonyl)amino}acetylamino)propionateAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 1.5 g of ethyl 3-aminopropionate monohydrochloride and 1.7 g of 2-{(tert-butoxycarbonyl)amino}acetic acid in 50 ml of chloroform, 1.6 g of 1-hydroxybenzotriazole monohydrate, 2.3 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide monohydrochloride and 1.4 ml of triethylamine were added at room temperature by the order stated, and stirred for 2 hours at the same temperature. The reaction liquid was diluted with chloroform, and washed successively with saturated aqueous sodium bicarbonate solution, 10% aqueous citric acid solution and saturated saline solution, by the order stated, and dried on anhydrous magnesium sulfate. The solvent was distlled off under reduced pressure, and the resultant residue was purified by means of silica gel column chromatography (eluting solvent: hexane/ethyl acetate=1/4) to provide 2.0 g of the title compound.

Aufarbeitung

  1. customThe reaction liquid
  2. washwashed successively with saturated aqueous sodium bicarbonate solution, 10% aqueous citric acid solution and saturated saline solution, by the order
  3. dry with materialdried on anhydrous magnesium sulfate
  4. customthe resultant residue was purified by means of silica gel column chromatography (eluting solvent: hexane/ethyl acetate=1/4)

Quellen und Nachweise

ORD-Eintrag
ord-28d8bbf7aa594d1590bdccfe5212e611
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452908B2

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