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

HRID 326882

반응식

HRID 326882 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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×)

출처 및 근거

ORD 기록
ord-22077298ca1f48d1a9f6e68022e8dc27
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05270464

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