4-Methylmorpholine → methyl(S)-N-[2-amino-3-nitro-5-(trifluoromethyl)benzoyl]alanine

HRID 1491624

Reaktionsgleichung

Reaktionsgleichung von HRID 1491624
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([C:14]([F:17])([F:16])[F:15])=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.[CH3:19][NH:20][C@H:21]([C:23]([OH:25])=[O:24])[CH3:22].O.ON1C2C=CC=NC=2C=N1.CN1CCOCC1>O1CCCC1>[CH3:19][N:20]([C:4](=[O:6])[C:3]1[CH:7]=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]=1[NH2:1])[C@H:21]([C:23]([OH:25])=[O:24])[CH3:22]

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 212519572-Amino-3-nitro-5-(trifluoromethyl)benzoic acidHCID 51064141(S)-2-(Methylamino)propanoic acid hydrochlorideHCID 701049091-hydroxy-1H-1,2,4-benzotriazole monohydrate

Produkt 1

HCID 70224754methyl(S)-N-[2-amino-3-nitro-5-(trifluoromethyl)benzoyl]alanineAusbeute 71,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a cooled (-5° C.) mixture of 20.0 parts of 2-amino-3-nitro-5-(trifluoromethyl)benzoic acid, 11.17 parts of methyl (S)-alanine monohydrochloride, 21.62 parts of 1-hydroxy-1H-1,2,4-benzotriazole monohydrate and 356 parts of tetrahydrofuran under argon there were added 8.1 parts of N-methylmorpholine and, after stirring for 10 min 16.5 parts of N,N-methanetetraylbis[cyclohexanamine]. Stirring was continued for 1 hour at -5° C. and overnight at room temperature. After cooling on ice, the reaction mixture was filtered and the filtrate was evaporated. The residue was dissolved in dichloromethane and this solution was washed with NaHCO3 (aq.), dried, filtered and evaporated. The residue was recrystallized from methylcyclohexane (2×), yielding 19.1 parts (71.2%) of methyl (S)-N-[2-amino-3-nitro-5-(trifluoromethyl)benzoyl]alanine; mp. 136.4° C. (interm. 33).

Aufarbeitung

  1. temperatureTo a cooled
  2. temperatureAfter cooling on ice
  3. filtrationthe reaction mixture was filtered
  4. customthe filtrate was evaporated
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washthis solution was washed with NaHCO3 (aq.)
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was recrystallized from methylcyclohexane (2×)

Quellen und Nachweise

ORD-Eintrag
ord-46101e5df66742019fdb4bfbe049d117
Quelldatensatz
uspto-grants-1994_12
Patentnummer
US05371079

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