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Benzylamine → tert-butyl (2R,5S)-5-(benzylcarbamoyl)-2-[2-(2-{[N-(methoxycarbonyl)-beta-phenyl-L-phenylalanyl]amino}phenyl)ethyl]morpholine-4-carboxylate

HRID 629702
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 629702
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([O:29][C:30]([N:32]1[CH2:37][C@@H:36]([CH2:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[NH:46][C:47](=[O:67])[C@H:48]([CH:54]([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[NH:49][C:50]([O:52][CH3:53])=[O:51])[O:35][CH2:34][C@H:33]1[C:68](O)=[O:69])=[O:31])([CH3:28])([CH3:27])[CH3:26].[CH2:71]([NH2:78])[C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1.N1C(C)=CC=CC=1C>CN(C=O)C.CCOC(C)=O>[CH2:71]([NH:78][C:68]([C@H:33]1[N:32]([C:30]([O:29][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:31])[CH2:37][C@@H:36]([CH2:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[NH:46][C:47](=[O:67])[C@H:48]([CH:54]([C:61]2[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=2)[C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[NH:49][C:50]([O:52][CH3:53])=[O:51])[O:35][CH2:34]1)=[O:69])[C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1
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Komponenten

7

Edukt 4

HCID 7504BenzylamineHCID 79372,6-LutidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86726308(3S,6R)-4-(tert-butoxycarbonyl)-6-[2-(2-{[N-(methoxycarbonyl)-beta-phenyl-L-phenylalanyl]amino}phenyl)ethyl]morpholine-3-carboxylic acid

Produkt 1

HCID 86726309
tert-butyl (2R,5S)-5-(benzylcarbamoyl)-2-[2-(2-{[N-(methoxycarbonyl)-beta-phenyl-L-phenylalanyl]amino}phenyl)ethyl]morpholine-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

HATU (1.4 eq) was added to a stirred mixture a solution of (3S,6R)-4-(tert-butoxycarbonyl)-6-[2-(2-{[N-(methoxycarbonyl)-β-phenyl-L-phenylalanyl]amino}phenyl)ethyl]morpholine-3-carboxylic acid (Example 1, step 11) (1 eq), benzyl amine (1.2 eq) and 2,6-lutidine (2 eq) in DMF (0.05 M) and the mixture was stirred at room temperature for 16 hrs. The mixture was diluted in EtOAc, The organic layer was washed with aqueous saturated NH4Cl and brine. The organic layer was dried over Na2SO4, filtered and evaporated. The residue was purified by automated silica gel flash chromatography system eluted with a gradient 10% to 100% of EtOAc/Hex to afford title compound.

Aufarbeitung

  1. washThe organic layer was washed with aqueous saturated NH4Cl and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by automated silica gel flash chromatography system
  6. washeluted with a gradient 10% to 100% of EtOAc/Hex

Quellen und Nachweise

ORD-Eintrag
ord-319db86de4f34e089f20a3714b07a5f8
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09315475B2

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