Sodium Carbonate → HCID 13652499, compound

Temperature

50 °C

To a solution of O-methyl-D,L-serine benzyl ester (50 mg, 0.239 mol) in 4-methyl-2-pentanone (500 mL) was added N-acetyl-L-methionine (45.7 g, 0.239 mol) at 25° C. The reaction mixture was heated to 50° C. and stirred for 2 hours, then allowed to cool to 25° C. and stirred for 16 hours at 25-30° C. The resulting solid material was filtered and dried at 60° C. for 3 hours. The mother liquors were evaporated. The isolated solid material (66 g) was dissolved in water (132 mL) at 25° C. The aqueous solution was basified with aqueous Na2CO3 solution (1M; 0.28 mol) at 5-10° C. The reaction mixture was extracted with dichloromethane (3×330 mL) at 25-30° C. The organic layer was dried over Na2SO4 and the solvent was evaporated under reduced pressure to afford O-methyl-D-serine benzyl ester as a light brown liquid (32.6 g, 66%). Chiral purity: 94.6%. Chemical purity: 98.3%.

1. temperatureto cool to 25° C.
2. stirringstirred for 16 hours at 25-30° C
3. filtrationThe resulting solid material was filtered
4. customdried at 60° C. for 3 hours
5. customThe mother liquors were evaporated
6. dissolutionThe isolated solid material (66 g) was dissolved in water (132 mL) at 25° C
7. extractionThe reaction mixture was extracted with dichloromethane (3×330 mL) at 25-30° C
8. dry with materialThe organic layer was dried over Na2SO4
9. customthe solvent was evaporated under reduced pressure

ORD record

ord-6f2c909d39b247cdb7d83a2cf9a66168

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139513B2