Morpholine → Tert-butyl 4-(morpholinomethyl)thiazol-2-ylcarbamate

Temperatur

0 °C

tert-Butyl 4-(hydroxymethyl)thiazol-2-ylcarbamate 89 (2.00 g, 8.68 mmol) was taken up in 25 mL of CH2Cl2 along with Et3N (1.82 mL, 13.05 mmol) and cooled to 0° C. Methanesulfonyl chloride (0.85 mL, 10.88 mmol) was added and the resulting reaction mixture was stirred at 0° C. for 60 min. Morpholine 63 (3.0 mL, 35 mmol) was then added and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated under reduced pressure. The resulting residue was taken up in EtOAc and washed with dilute aqueous NaHCO3, brine, dried with Na2SO4, and concentrated under reduced pressure. This material was purified by filtering through a short column of silica gel. The filtrate was concentrated to afford 90 (1.88 g, 69% yield).

1. customthe resulting reaction mixture
2. stirringthe reaction mixture was stirred at room temperature for 18 h
3. concentrationThe reaction mixture was concentrated under reduced pressure
4. washwashed with dilute aqueous NaHCO3, brine
5. dry with materialdried with Na2SO4
6. concentrationconcentrated under reduced pressure
7. customThis material was purified
8. filtrationby filtering through a short column of silica gel
9. concentrationThe filtrate was concentrated

ORD-Eintrag

ord-ded2a1763b7646699b6e7d47fecf5e4c

Quelldatensatz

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09326986B2