1,2-Dichloroethane → N-(t-Butoxycarbonyl)-D-homophenylalanine allyl ester

HRID 1913

Reaktionsgleichung

Reaktionsgleichung von HRID 1913
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:18]([OH:20])=[O:19])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21](O)[CH:22]=[CH2:23].C(Cl)CCl>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:23]([O:19][C:18](=[O:20])[C@@H:9]([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:22]=[CH2:21]

Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 7858Allyl AlcoholHCID 2755954Boc-D-homophenylalanine

Produkt 1

HCID 22883348N-(t-Butoxycarbonyl)-D-homophenylalanine allyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-(t-Butoxycarbonyl)-D-homophenylalanine (2.0 g; 7.16 mmol), allyl alcohol (500 ml; 7.35 mmol) and 4-dimethylaminopyridine (88 mg; 0.72 mmol) were dissolved in dry methylene chloride and stirred at room temperature. EDC (1.4 g; 7.30 mmol) was added to the solution in small batches over 15 minutes and the reaction mixture stirred at room temperature for 6 h. The reaction was quenched by pouring the reaction mixture into water (10 ml) and extracted with methylene chloride (2×25 ml). The combined methylene chloride extracts were washed successively with 5% aqueous citric acid solution (50 ml) and a 10% aqueous sodium carbonate solution. The methylene chloride layer was dried over anhydrous magnesium surf ate powder, filtered and evaporated to leave a thick oily residue which was purified by column chromatography on silica gel using an eluant comprising ethyl acetate and hexanes in the ratio 2:1. The yield of the desired allyl ester product was 1.96 g (85.7%). FAB-MS:- calculated for C18 H25NO4 319.2; found 320. (M+1).

Aufarbeitung

  1. stirringthe reaction mixture stirred at room temperature for 6 h
  2. customThe reaction was quenched
  3. additionby pouring the reaction mixture into water (10 ml)
  4. extractionextracted with methylene chloride (2×25 ml)
  5. washThe combined methylene chloride extracts were washed successively with 5% aqueous citric acid solution (50 ml)
  6. dry with materialThe methylene chloride layer was dried over anhydrous magnesium surf
  7. filtrationfiltered
  8. customevaporated
  9. customto leave a thick oily residue which
  10. customwas purified by column chromatography on silica gel using an eluant comprising ethyl acetate and hexanes in the ratio 2:1

Quellen und Nachweise

ORD-Eintrag
ord-dbb9dc3e9fc84d65b7962d36a9ed7bea
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726319

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