Triphosgene → HCID 58091390, Verbindung

HRID 2045691Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2045691
[C:1]([O-])(O)=[O:2].[Na+].Cl.[NH2:7][C@@H:8]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:9]([O:11][CH3:12])=[O:10].ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH:13]1([C@H:8]([N:7]=[C:1]=[O:2])[C:9]([O:11][CH3:12])=[O:10])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Komponenten

5

Edukt 3

HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 17747951(S)-Methyl 2-amino-2-cyclohexylacetate hydrochloride

Produkt 1

HCID 58091390HCID 58091390, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 500 mL round-bottom flask was charged with saturated NaHCO3 (80 mL) and DCM (80 ml) and cooled in an ice bath with vigorous stirring. Methyl (2S)-amino(cyclohexyl)acetate hydrochloride (4.0 g, 19.26 mmol) was added followed by triphosgene (1.886 g, 6.36 mmol). The contents of the reaction flask were stirred for 1 hr with cooling, then poured into a reparatory funnel. The layers were separated, and the aqueous layers were extracted with 20 mL DCM. The combined organic portions were dried with anhydrous MgSO4, filtered and evaporated to give the title compound as a colorless oil. 1H NMR (CDCl3): δ 3.90 (d, J 4, 1H), 3.81 (s, 3H), 1.88-1.83 (m, 1H), 1.79-1.76 (m, 2H), 1.69-1.62 (m, 2H), 1.54-1.48 (m, 1H), 1.29-1.11 (m, 5H) ppm.

Aufarbeitung

  1. temperaturecooled in an ice bath with vigorous stirring
  2. temperaturewith cooling
  3. additionpoured into a reparatory funnel
  4. customThe layers were separated
  5. extractionthe aqueous layers were extracted with 20 mL DCM
  6. dry with materialThe combined organic portions were dried with anhydrous MgSO4
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-864feaddfa054d1984467162635da692
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08591878B2

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