Ethyl chloroacetate → ethyl N-{(1S,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentyl}glycinate

HRID 81188

Reaktionsgleichung

Reaktionsgleichung von HRID 81188
[NH2:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>C(#N)C>[C:10]([O:9][C:8]([NH:7][C@H:3]1[CH2:4][CH2:5][CH2:6][C@@H:2]1[NH:1][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:14])([CH3:11])([CH3:13])[CH3:12]

Komponenten

5

Edukt 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 17040218(1S,2S)-trans-N-Boc-1,2-cyclopentanediamine

Produkt 1

HCID 86724541ethyl N-{(1S,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentyl}glycinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

tert-Butyl [(1S,2S)-2-aminocyclopentyl]carbamate (900 mg, 4.49 mmol) (purchased from Sigma Aldrich) was taken up in acetonitrile (13 mL). Potassium carbonate (932 mg, 6.74 mmol) and ethyl chloroacetate (0.577 mL, 5.39 mmol) were added, and the resulting mixture was heated to 55° C. overnight. The resulting mixture was cooled to room temperature and concentrated under reduced pressure. The residue was taken up in EtOAc, washed with water and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (0-100% EtOAc/hexanes) to afford ethyl N-{(1S,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentyl}glycinate.

Aufarbeitung

  1. temperatureThe resulting mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (0-100% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-be2625effce94f9c8aa6c25fd372ad58
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846657B2

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