Sulfuric Acid → N-carbobenzoxy-D-alanine(1-methyl-1-cyclopentyl)ester

HRID 35443

Reaktionsgleichung

Reaktionsgleichung von HRID 35443
[C:1]([NH:11][C@@H:12]([C:14]([OH:16])=[O:15])[CH3:13])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].S(=O)(=O)(O)O.[CH3:22][C:23]1[CH2:27][CH2:26][CH2:25][CH:24]=1>ClCCl>[CH3:22][C:23]1([O:15][C:14](=[O:16])[C@@H:12]([CH3:13])[NH:11][C:1]([O:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:2])[CH2:27][CH2:26][CH2:25][CH2:24]1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 127461-MethylcyclopenteneHCID 70832N-Cbz-d-alanine

Produkt 1

HCID 22839475N-carbobenzoxy-D-alanine(1-methyl-1-cyclopentyl)ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a magnetically stirred solution of 22.3 g (0.1 mol) N-Cbz-D-alanine in 50 mls of dry dichloromethane containing 0.5 mls of concentrated sulfuric acid at 0° C., was added dropwise a 10 g (0.1 mol) sample of 1-methylcyclopentene in 50 mls of dichloromethane. After 5 days of stirring at room temperature, the mixture was heated to reflux for 4 hours, after which the reaction was cooled to room temperature, washed with 100 mls of saturated NaHCO3, 100 mls of water and dried over MgSO4. Filtration followed by evaporation of the solvent yielded 1.81 g of the product. NMR(CDCl3): δ1.3-1.4(d, 3H), 1.5(s, 3H), 1.5-1.7 (m, 8H), 4.2 (m, 1H), 5.05 (s, 2H), 5.25 (m, 1H), 7.3 (s, 5H).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. temperatureafter which the reaction was cooled to room temperature
  4. washwashed with 100 mls of saturated NaHCO3, 100 mls of water
  5. dry with materialdried over MgSO4
  6. filtrationFiltration
  7. customfollowed by evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-7c5d170a29c34f9494571d4c21b41012
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04766246

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