3,3,3-Triphenylpropionic Acid → Ethyl 3-(2-{(3,3,3-triphenylpropanoyl)amino}acetylamino)propionate

HRID 272062Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 272062
Cl.[NH2:2][CH2:3][C:4]([NH:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:5].[C:14]1([C:20]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21][C:22](O)=[O:23])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)(Cl)Cl.C(OCC)(=O)C.C(N(CC)CC)C>[C:31]1([C:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:21][C:22]([NH:2][CH2:3][C:4]([NH:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:5])=[O:23])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Komponenten

8

Edukt 4

HCID 1366963,3,3-Triphenylpropionic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22647362Ethyl 3-{(2-aminoacetyl)amino}propionate monohydrochloride

Produkt 1

HCID 22647252Ethyl 3-(2-{(3,3,3-triphenylpropanoyl)amino}acetylamino)propionateAusbeute 51,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6212ChloroformLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1.52 g of ethyl 3-{(2-aminoacetyl)amino}-propionate monohydrochloride and 2.18 g of 3,3,3-triphenylpropionic acid in 20 ml of chloroform, 1.46 g of 1-hydroxybenzotriazole monohydrate, 2.07 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide monohydrochloride and 2.0 ml of triethylamine were successively added at room temperature by the order stated, followed by 2 hours' stirring at the same temperature. The reaction liquid was diluted with ethyl acetate and washed successively with aqueous saturated sodium bicarbonate solution, 1N-hydrochloric acid and water, and filtered through cerite. The filtrate was dried on anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was purified by means of silica gel column chromatography (eluting solvent: hexane/ethyl acetate=4/1-chloroform/methanol=10/1) to provide 1.7 g of the title compound.

Aufarbeitung

  1. customThe reaction liquid
  2. washwashed successively with aqueous saturated sodium bicarbonate solution, 1N-hydrochloric acid and water
  3. filtrationfiltered through cerite
  4. dry with materialThe filtrate was dried on anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resultant residue was purified by means of silica gel column chromatography (eluting solvent: hexane/ethyl acetate=4/1-chloroform/methanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-e12c7310f7f14837974b84085aecb64f
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452908B2

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