Hydrochloric Acid → (S)-tert-butyl 4-chloro-1-cyclohexyl-3-oxobutan-2-ylcarbamate

HRID 253558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 253558
[CH:1]1([CH2:7][C@H:8]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:9](=[O:13])[CH:10]=[N+]=[N-])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:22].O1CCOCC1>CCOCC>[Cl:22][CH2:10][C:9](=[O:13])[C@@H:8]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86632797(S)-tert-butyl 1-cyclohexyl-4-diazo-3-oxobutan-2-ylcarbamate

Produkt 1

HCID 10063585(S)-tert-butyl 4-chloro-1-cyclohexyl-3-oxobutan-2-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of the crude (S)-tert-butyl 1-cyclohexyl-4-diazo-3-oxobutan-2-ylcarbamate (7 g, ˜65% pure) in anhydrous ether (150 mL) at 0° C. was added dropwise a solution of 3.65 N HCl in dioxane (4.1 mL, 0.015 mmol). The mixture was stirred until tlc showed the starting material had been consumed. Satd aq NaHCO3 was added and the organic layer was separated, washed with satd aq NaHCO3 and brine, and concentrated to afford a solution of crude (S)-tert-butyl 4-chloro-1-cyclohexyl-3-oxobutan-2-ylcarbamate (5.8 g), which was used in the next step without further purification.

Aufarbeitung

  1. customhad been consumed
  2. additionSatd aq NaHCO3 was added
  3. customthe organic layer was separated
  4. washwashed with satd aq NaHCO3 and brine
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-21ba1a6383164a4a8c27599e92771c4f
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872028B2

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