Methanol → HCID 52180852, Verbindung

HRID 1808791Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1808791
[N:1]1([C:5](=[O:18])[C@@H:6]([NH:10]C(=O)OC(C)(C)C)[CH:7]([CH3:9])[CH3:8])[CH2:4][CH2:3][CH2:2]1.O1CCOCC1.CO>Cl>[NH2:10][C@@H:6]([CH:7]([CH3:9])[CH3:8])[C:5]([N:1]1[CH2:4][CH2:3][CH2:2]1)=[O:18]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 312751,4-Dioxane2×HCID 52180842tert-Butyl [(2S)-1-(azetidin-1-yl)-3-methyl-1-oxobutan-2-yl]carbamate2×

Produkt 1

HCID 52180852HCID 52180852, VerbindungAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel2×

Versuchsvorschrift

(S)-Tert-butyl 1-(azetidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (Compound D) (23.56 g, 90.07 mmol) was stirred in 4M HCl in dioxane (56.3 mL, 225 mmol) for 30 min. Additional dioxane and MeOH was added until the reaction mixture became a clear solution. The solvent was removed under reduced pressure and conc. HCl (3.00 mL, 30.4 mmol) was added. The mixture was stirred for 5 h before the solvent was removed. The residue was purified via Biotage (gradient; EtOAc:MeOH (2% TEA), 99:1 to 90:10, then EtOAc:MeOH (2% TEA) 90:10 to 0/100 KP-SIL 340 g. The solvent was removed under reduced pressure to give the title compound (10.3 g, 70.3%). 1H NMR (600 MHz, CH3OD) δ 1.03, 1.06, 2.07-2.16, 2.33-2.41, 3.71, 3.99-4.07, 4.07-4.14, 4.25-4.33, 4.33-4.41. Total no of protons: 14. LCMS (M+H)+: 157.

Aufarbeitung

  1. additionwas added
  2. customwas removed
  3. customThe residue was purified via Biotage (gradient
  4. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0e50734ca9494ec0b771495786ae106d
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08361998B2

Notizen zur Reaktion

Wird geladen…