Benzyl chloroformate → Carbobenzoxyhomoserine

HRID 556387

Reaktionsgleichung

Reaktionsgleichung von HRID 556387
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][OH:5].Cl[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]>O1CCOCC1>[CH2:13]([O:12][C:10]([NH:1][C@H:2]([CH2:3][CH2:4][OH:5])[C:6]([OH:8])=[O:7])=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

4

Edukt 2

HCID 10387Benzyl chloroformateHCID 12647L-Homoserine

Produkt 1

HCID 193811Carbobenzoxyhomoserine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To an ice-cooled solution of H-Hse-OH (5 g) in dioxane/2M NaOH (168 mL/42 mL) was added benzyl chloroformate (6.7 mL) dropwise over 15 min. The reaction mixture was allowed to warm to RT and was stirred overnight at RT. The solvent was evaporated off and the aq. residue was extracted with Et2O and acidified with a 2M HCl solution. The aq. phase was extracted with DCM. The DCM layers were combined, washed with water, dried (Na2SO4) and evaporated off to give the desired product as a white powder (6.2 g).

Aufarbeitung

  1. customThe solvent was evaporated off
  2. extractionthe aq. residue was extracted with Et2O
  3. extractionThe aq. phase was extracted with DCM
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated off

Quellen und Nachweise

ORD-Eintrag
ord-b1cfcd14a8e5412eb115fc2fc66c5adf
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058263B2

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