Methyl N-benzyloxycarbonylglycinate → HCID 11414679, compound

Temperature

70 °C

Toluene (10 ml) was added to N-benzyloxycarbonyl-glycine methyl ester (1.50 g, 6.73 mmol) and tert-butoxybisdimethylaminomethane (1.83 ml, 8.91 mmol) and the mixture was stirred overnight at 70° C. The mixture was washed with saturated brine and concentrated under reduced pressure. MTBE (20 ml) and 1N hydrochloric acid (15 ml) were added to the residue in an ice bath and the mixture was stirred at room temperature for 2 hr. Thereafter, the mixture was separated and the organic layer was washed with saturated brine. A solution (1.23 g, 6.39 mmol) of 28% sodium methoxide in methanol was added drop-wise and the mixture was concentrated under reduced pressure. The solvent was substituted by acetonitrile and O-methylisourea hydrochloride (0.72 g, 6.50 mmol) was added. The mixture was stirred overnight at 70° C. and concentrated. Water (5 ml) was added and the mixture was stirred for 1 hr. The precipitate was collected by filtration and vacuum dried to give 2-methoxy-6-oxo-5-benzyloxycarbonylamino-1,6-dihydropyrimidine (1.43 g, 5.20 mmol).

1. washThe mixture was washed with saturated brine
2. concentrationconcentrated under reduced pressure
3. additionMTBE (20 ml) and 1N hydrochloric acid (15 ml) were added to the residue in an ice bath
4. stirringthe mixture was stirred at room temperature for 2 hr
5. customThereafter, the mixture was separated
6. washthe organic layer was washed with saturated brine
7. concentrationthe mixture was concentrated under reduced pressure
8. additionwas added
9. stirringThe mixture was stirred overnight at 70° C.
10. concentrationconcentrated
11. additionWater (5 ml) was added
12. stirringthe mixture was stirred for 1 hr
13. filtrationThe precipitate was collected by filtration and vacuum
14. customdried

ORD record

ord-842a3aa7bb76466793cc67e65e645878

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07507738B2