4-Methylmorpholine → (-)-methyl(S)-2-[(2-amino-3-nitrobenzoyl)amino]propanoate

温度

0 °C

To a stirred and cooled (-12° C.) mixture of 9.10 parts of 2-amino-3-nitrobenzoic acid, 6.95 parts of methyl L-α-alanine monohydrochloride, 13.50 parts of 1-hydroxy-1H-1,2,4-benzotriazole monohydrate and 178 parts of tetrahydrofuran there were added portionwise 5.05 parts of N-methylmorpholine and, after 5 min, 10.3 parts of N,N'-methanetetraylbis[cyclohexanamine] under an argon atmosphere. Stirring was continued for 51/2 hours at -12° C. and for 15 hours at room temperature. After cooling to 0° C. for 1/2 hour, the reaction mixture was filtered and the filtrate was evaporated. The residue was partitioned between ethyl acetate and a saturated sodium hydrogen carbonate solution. The organic layer was separated, washed with NaHCO3 (sat.), dried, filtered and evaporated. The residue was triturated with hexane. The product was filtered off and dried, yielding 13.08 parts (97.9%) of (-)-methyl (S)-2-[(2-amino-3-nitrobenzoyl)amino]propanoate; mp. 132.9° C. (interm. 24).

1. temperaturecooled
2. stirringStirring
3. custom2 hours
4. customat -12° C.
5. waitfor 15 hours at room temperature
6. filtrationthe reaction mixture was filtered
7. customthe filtrate was evaporated
8. customThe residue was partitioned between ethyl acetate
9. customThe organic layer was separated
10. washwashed with NaHCO3 (sat.)
11. customdried
12. filtrationfiltered
13. customevaporated
14. customThe residue was triturated with hexane
15. filtrationThe product was filtered off
16. customdried

ORDレコード

ord-bb1c76f9d7e444c5bbcb5c9b9a92608a

出典データセット

uspto-grants-1994_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05371079