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Benzoic Acid → tert-butyl (2R,5R)-2-[2-(2-{[N-(methoxycarbonyl)-beta-phenyl-L-phenylalanyl]amino}phenyl)ethyl]-5-{[(phenylcarbonyl)amino]methyl}morpholine-4-carboxylate

HRID 629717
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 629717
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:25][CH2:26][C@H:27]1[N:32]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31][C@@H:30]([CH2:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=2[NH:48][C:49](=[O:69])[C@H:50]([CH:56]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[NH:51][C:52]([O:54][CH3:55])=[O:53])[O:29][CH2:28]1.[C:70](O)(=[O:77])[C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1.N1C(C)=CC=CC=1C>CN(C=O)C.CCOC(C)=O>[CH3:55][O:54][C:52]([NH:51][C@H:50]([C:49]([NH:48][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=1[CH2:41][CH2:40][C@H:30]1[O:29][CH2:28][C@@H:27]([CH2:26][NH:25][C:70]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)=[O:77])[N:32]([C:33]([O:35][C:36]([CH3:38])([CH3:39])[CH3:37])=[O:34])[CH2:31]1)=[O:69])[CH:56]([C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)=[O:53]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 243Benzoic AcidHCID 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 86726318tert-butyl (2R,5R)-5-(aminomethyl)-2-[2-(2-{[N-(methoxycarbonyl)-beta-phenyl-L-phenylalanyl]amino}phenyl)ethyl]morpholine-4-carboxylate

Produkt 1

HCID 86726321
tert-butyl (2R,5R)-2-[2-(2-{[N-(methoxycarbonyl)-beta-phenyl-L-phenylalanyl]amino}phenyl)ethyl]-5-{[(phenylcarbonyl)amino]methyl}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 tert-butyl (2R,5R)-5-(aminomethyl)-2-[2-(2-{[N-(methoxycarbonyl)-β-phenyl-L-phenylalanyl]amino}phenyl)ethyl]morpholine-4-carboxylate (1 eq), benzoic acid (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-c905608802e1452aae03d8e16cc1bedc
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09315475B2

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