Diethyl Ether → HCID 54393776, Verbindung

HRID 617757Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 617757
Cl.[CH3:2][C@H:3]([NH2:13])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[OH-].[Na+].[CH2:16]([O:23][C:24](Cl)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCOCC>CC(C)=O>[C:24]([NH:13][C@@H:3]([CH3:2])[C:4]1[CH:5]=[CH:6][C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=1)([O:23][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:25]

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 16212176(1S)-1-(4-Nitrophenyl)ethan-1-amine--hydrogen chloride (1/1)

Produkt 1

HCID 54393776HCID 54393776, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

To a solution of (S)-(-)-α-methyl-4-nitrobenzylamine hydrochloride (7.96 gm, 48 mmol) in acetone (20 mL) was added 5N sodium hydroxide (10 mL, 50 imol) and the solution was cooled in an ice bath. Solutions of benzylchloroformate (9.8 mL, 53 mmol) in acetone (10 mL) and 5N sodium hydroxide (11 mL, 55 mmol) were simultaneously added over 0.5 hr and the reaction was then allowed to warm to rt over 16 hrs. The reaction was poured into a mixture of ice water and ether and the layers were separated. The ether layer was washed with water and brine and the aqueous layers were consecutively extracted with a second portion of ether. The pooled ether layers were dried over sodium sulfate and evaporated to give 14.3 gm (quantitative) of clean title compound which was used without purification.

Aufarbeitung

  1. temperaturethe solution was cooled in an ice bath
  2. customthe layers were separated
  3. washThe ether layer was washed with water and brine
  4. extractionthe aqueous layers were consecutively extracted with a second portion of ether
  5. dry with materialThe pooled ether layers were dried over sodium sulfate
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-13d3dbf0aa6547c792aebdea151aa25b
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952321

Notizen zur Reaktion

Wird geladen…