4-Methylmorpholine → HCID 940643, compound

HCL-Valine methyl ester (25 g) was dissolved under argon in 600 mL of freshly distilled THF and 100 mL of dry DMF and 1.0 equivalents of N-methyl morpholine. The resulting solution was cooled to -15° and an additional 1.1 equivalent of N-methyl morpholine followed by 1.1 equivalents of morpholine chloride was added. The reaction was allowed to come slowly to room temperature and stir overnight. The reaction is then poured into 300 mL of 1N HCL and extracted with ethyl acetate (2×200 mL). The combined organic fractions were washed with 1N HCL (50 mL), brine (50 mL), dried over MgSO4, filtered and the solvents were removed under reduced pressure to give 33 g of N-morpholinecarbonyl-valine methyl ester as a white solid: NMR (100 MHz, CDCl3 δ 0.9 (dd, 6), 2.1 (septet, 1), 3.0 and 3.65 (morpoline triplets, 4 and 4), 4.98 (N-H).

1. temperatureThe resulting solution was cooled to -15°
2. additionwas added
3. customto come slowly to room temperature
4. additionThe reaction is then poured into 300 mL of 1N HCL
5. extractionextracted with ethyl acetate (2×200 mL)
6. washThe combined organic fractions were washed with 1N HCL (50 mL), brine (50 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. customthe solvents were removed under reduced pressure

ORD record

ord-1ec53c08cb1b4c988ff0697452fa207a

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06147188