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4-Methylmorpholine → methyl N-[(1S)-1-[[(1S,2S)-1-benzyl-2-hydroxy-3-[[[(2S,3S)-2-(methoxycarbonylamino)-3-methyl-pentanoyl]amino]-[(4-pyrazin-2-ylphenyl)methyl]amino]propyl]carbamoyl]-2-methyl-propyl]carbamate

HRID 1458479
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1458479
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:11]([OH:13])=O)[C@H:7]([CH2:9][CH3:10])[CH3:8])=[O:4].[B-](F)(F)(F)F.CN(C(ON1[C:32](=[O:33])C=CC=C1)=[N+](C)C)C.Cl.[N:35]1[CH:40]=[CH:39][N:38]=[CH:37][C:36]=1[C:41]1[CH:46]=[CH:45][C:44]([CH2:47][N:48]([NH2:72])[CH2:49][C@H:50]([OH:71])[C@@H:51]([NH:59][C:60](=[O:70])[C@H:61]([CH:65]([CH3:69])[CH:66]=C=O)[NH:62]OC)[CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[CH:43][CH:42]=1.CN1CC[O:77][CH2:76]C1>CN(C=O)C.C(OCC)(=O)C.O1CCOCC1.O>[N:35]1[CH:40]=[CH:39][N:38]=[CH:37][C:36]=1[C:41]1[CH:42]=[CH:43][C:44]([CH2:47][N:48]([NH:72][C:11](=[O:13])[C@H:6]([C@H:7]([CH2:9][CH3:10])[CH3:8])[NH:5][C:3]([O:2][CH3:1])=[O:4])[CH2:49][C@H:50]([OH:71])[C@@H:51]([NH:59][C:60](=[O:70])[C@H:61]([CH:65]([CH3:69])[CH3:66])[NH:62][C:76]([O:33][CH3:32])=[O:77])[CH2:52][C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)=[CH:45][CH:46]=1
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Komponenten

9

Edukt 4

HCID 79724-MethylmorpholineHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 28378062L-Isoleucine, N-(methoxycarbonyl)-HCID 867534571-[4-(pyrazin-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxy-carbonyl-(L)-valyl)amino-6-phenyl-2-azahexane hydrochloride

Produkt 1

HCID 467983
methyl N-[(1S)-1-[[(1S,2S)-1-benzyl-2-hydroxy-3-[[[(2S,3S)-2-(methoxycarbonylamino)-3-methyl-pentanoyl]amino]-[(4-pyrazin-2-ylphenyl)methyl]amino]propyl]carbamoyl]-2-methyl-propyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

142 mg (0.75 mmol) of N-methoxycarbonyl-(L)-iso-leucine and 223 mg (0.75 mmol) of TPTU in 3 ml of DMF are stirred at room temperature for 10 min and then a solution of 473 mg (0.75 mmol) of 1-[4-(pyrazin-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxy-carbonyl-(L)-valyl)amino-6-phenyl-2-azahexane hydrochloride (Example 40g) and 0.33 ml of NMM in 3 ml of DMF is added. The mixture is stirred at room temperature overnight. Working up is carried out by the slow, dropwise addition of the reaction mixture to 100 ml of water, stirring at room temperature for 20 min and isolation of the resulting precipitate by filtration. The precipitate is washed with water and taken up in methylene chloride; the organic phase is washed in succession with water, sat. sodium hydrogen carbonate solution/water 1:1, water and brine. After removal of the solvent, the residue is digested in ether, with the title compound being obtained in the form of a colourless powder. The compound can be lyophilised from dioxane. TLC: Rt =0.28 (ethyl acetate). HPLC20-100 : tRet =13.78. FAB MS(M+H)+ =692.

Aufarbeitung

  1. stirringstirring at room temperature for 20 min
  2. filtrationisolation of the resulting precipitate by filtration
  3. washThe precipitate is washed with water
  4. washthe organic phase is washed in succession with water, sat. sodium hydrogen carbonate solution/water 1:1, water and brine
  5. customAfter removal of the solvent
  6. custombeing obtained in the form of a colourless powder

Quellen und Nachweise

ORD-Eintrag
ord-81adc052fa644d27b6193dc76d80edd3
Quelldatensatz
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05849911

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