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

HRID 326881

Reaktionsgleichung

Reaktionsgleichung von HRID 326881
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[OH2:14].ON1[C:20]2C=CC=[N:24][C:19]=2[CH:18]=N1.CN1C[CH2:30][O:29]CC1>O1CCCC1>[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:24][C@@H:19]([CH3:18])[C:20]([O:29][CH3:30])=[O:14])=[O:6]

Komponenten

5

Edukt 3

HCID 79724-MethylmorpholineHCID 2196332-Amino-3-nitrobenzoic acidHCID 701049091-hydroxy-1H-1,2,4-benzotriazole monohydrate

Produkt 1

HCID 14879834(-)-methyl(S)-2-[(2-amino-3-nitrobenzoyl)amino]propanoateAusbeute 97,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c19f32f72d1443ba8384e9a57f759ed8
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05270464

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