Potassium Hydroxide → erythro-N-Boc-D-phenylalanine epoxide

HRID 424978

Reaktionsgleichung

Reaktionsgleichung von HRID 424978
[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C@@H:9]([OH:12])[CH2:10]Cl)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>C(O)C>[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]([C@@H:9]1[CH2:10][O:12]1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 60170213HCID 60170213, Verbindung

Produkt 1

HCID 11357515erythro-N-Boc-D-phenylalanine epoxideAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of (R,R)-1-benzyl-3-chloro-2-hydroxypropylcarbamic acid tert-butyl ester (4.45 g, 15 mmol) in ethanol (125 mL) at 0° C. is added KOH (0.5M in ethanol, 36 ml, 18 mmol). After stirring for 20 min, the mixture is concentrated under reduced pressure and the residue is dissolved in ethyl acetate, washed with saturated ammonium chloride (aq), water and then brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting white solid is purified using General Purification Procedure E to afford the title compound as a white solid (2.7 g, 10.4 mmol).

Aufarbeitung

  1. concentrationthe mixture is concentrated under reduced pressure
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washwashed with saturated ammonium chloride (aq), water
  4. dry with materialbrine, dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting white solid is purified
  7. customGeneral Purification Procedure E

Quellen und Nachweise

ORD-Eintrag
ord-2f53e88e4ec4460b9f8801f6c321376e
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106090B2

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