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

HRID 326882

反応式

HRID 326882 の反応式
[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]

参加物

6

反応物 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

生成物 1

HCID 70224754methyl(S)-N-[2-amino-3-nitro-5-(trifluoromethyl)benzoyl]alanine収率 71.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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×)

出典と根拠

ORDレコード
ord-22077298ca1f48d1a9f6e68022e8dc27
出典データセット
uspto-grants-1993_12
特許番号
US05270464

関連ノート

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