Triphosgene → HCID 58158056, Verbindung

HRID 1255508Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1255508
Cl.[NH2:2][C@@H:3]([CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)[C:4]([O:6][CH3:7])=[O:5].Cl[C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH:8]1([C@H:3]([N:2]=[C:14]=[O:16])[C:4]([O:6][CH3:7])=[O:5])[CH2:12][CH2:11][CH2:10][CH2:9]1

Komponenten

5

Edukt 2

HCID 94429TriphosgeneHCID 51358379Methyl (2S)-amino(cyclopentyl)acetate--hydrogen chloride (1/1)

Produkt 1

HCID 58158056HCID 58158056, VerbindungAusbeute 215,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A suspension of methyl (25)-amino(cyclopentyl)acetate hydrochloride (3.21 g, 16.57 mmol) in DCM (69 mL) and saturated NaHCO3(aq.) (132 mL) was cooled to 0° C. and treated with triphosgene (2.21 g, 7.46 mmol). The mixture was stirred at 0° C. for 3 hours, then warmed to 20° C. and diluted with DCM. The layers were separated, and the aqueous phase was re-extracted with DCM. The combined organic phases were washed with brine and dried over Na2SO4. Filtration and removal of the volatiles afforded the title compound (2.95 g, 97%) as an oily solid that was used directly in subsequent steps. 1H NMR (400 MHz, DMSO-d6) δ 4.36 (d, J=4.8 Hz, 1H), 3.73 (s, 1H), 2.35-2.24 (m, 1H), 1.76-1.24 (m, 8H).

Aufarbeitung

  1. temperaturewarmed to 20° C.
  2. customThe layers were separated
  3. extractionthe aqueous phase was re-extracted with DCM
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationFiltration and removal of the volatiles

Quellen und Nachweise

ORD-Eintrag
ord-2fa8c94106a04d768cbb37218a89e469
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461107B2

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