4-Methylmorpholine → N-[(3-benzyl-3-azabicyclo[3.1.0]hex-6-yl carbamoyl)-methyl]-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propionamide

HRID 2110551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2110551
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:10][C:11]([OH:13])=O.[NH2:20][CH2:21][C:22]([NH:24][CH:25]1[CH:30]2[CH:26]1[CH2:27][N:28]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:29]2)=[O:23].C(OC(NCC(O)=O)=O)(C)(C)C.C(N1CC2C(C2N)C1)C1C=CC=CC=1.CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O.O>[CH2:31]([N:28]1[CH2:27][CH:26]2[CH:30]([CH:25]2[NH:24][C:22]([CH2:21][NH:20][C:11](=[O:13])[CH2:10][CH:9]([C:3]2[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=2[OH:1])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:23])[CH2:29]1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Komponenten

9

Edukt 6

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 125220763-(2-Hydroxy-5-methylphenyl)-3-phenyl propionic acidHCID 185069973-Benzyl-3-azabicyclo(3.1.0)hexan-6-amineHCID 688714602-amino-N-(3-benzyl-3-azabicyclo[3.1.0]hex-6-yl)-acetamide

Produkt 1

HCID 68870343N-[(3-benzyl-3-azabicyclo[3.1.0]hex-6-yl carbamoyl)-methyl]-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propionamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The compound, 3-(2-hydroxy-5-methylphenyl)-3-phenyl propionic acid (198 mg, 0.77 mmole, 1 eq) and 2-amino-N-(3-benzyl-3-azabicyclo[3.1.0]hex-6-yl)-acetamide, 200 mg, 0.179 mmole, 1 eq prepared by reacting t-butoxy carbonylamino-acetic acid with 3-benzyl-3-azabicylo[3.1.0]hex-6-yl amine, which in turn, was prepared following the procedure of T. F. Braish et al., Synlett, 1996, 1100) were dissolved in dimethylformamide (3 ml). The reaction mixture was cooled to 0° C. with subsequent addition of N-methyl morpholine (2.31 mmole, 3 eq) and HOBT (0.77 mmole, 1 eq). The resulting reaction mixture was stirred for 1 hour at the same temperature and then at room temperature. The reaction mixture was diluted with water and extracted the organic compound with ethyl acetate. The solvent was removed under reduced pressure and dried. The crude compound was purified by column chromatography using ethyl acetate, methanol and dichloromethane solvent system.

Aufarbeitung

  1. customwas prepared
  2. customThe resulting reaction mixture
  3. customat room temperature
  4. extractionextracted the organic compound with ethyl acetate
  5. customThe solvent was removed under reduced pressure
  6. customdried
  7. customThe crude compound was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5051d87ec9f945ac8a6165eb78ae3f80
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517905B2

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