Eugenol → Amino-acetic acid 4-allyl-2-methoxy-phenyl ester

HRID 82490

Reaktionsgleichung

Reaktionsgleichung von HRID 82490
[C:1]1([O:11][CH3:12])[C:2](=[CH:4][CH:5]=[C:6]([CH:10]=1)[CH2:7][CH:8]=[CH2:9])[OH:3].C([NH:20][CH2:21][C:22](O)=[O:23])(OC(C)(C)C)=O.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:7]([C:6]1[CH:5]=[CH:4][C:2]([O:3][C:22](=[O:23])[CH2:21][NH2:20])=[C:1]([O:11][CH3:12])[CH:10]=1)[CH:8]=[CH2:9]

Komponenten

7

Edukt 4

HCID 3314EugenolHCID 79724-MethylmorpholineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 69920127Amino-acetic acid 4-allyl-2-methoxy-phenyl esterAusbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of Eugenol (0.3 g, 1.82 mmol) in DCM (20 mL), was added Boc-glycine (0.35 g, 2.01 mmol), N-methyl morpholine (0.65 mL, 6.00 mmol), EDC.HCl (0.76 g, 4.0 mmol) and DMAP at ice temperature. The mixture was allowed to stir at room temperature (25° C.) over a period of 12 h. The resulting mixture was diluted with DCM (100 mL), washed with water (2×50 mL) and dried over sodium sulphate. The crude product obtained upon evaporation of the solvent was purified by silica gel column chromatography to obtain resulting product as pale yellow oil (300 mg, 46.9%)

Aufarbeitung

  1. washwashed with water (2×50 mL)
  2. dry with materialdried over sodium sulphate
  3. customThe crude product obtained upon evaporation of the solvent
  4. customwas purified by silica gel column chromatography
  5. customto obtain

Quellen und Nachweise

ORD-Eintrag
ord-20563f5d9d02499d865f4a5bbbe742c0
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846721B2

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