Hydrochloric Acid → HCID 178471713, Verbindung

HRID 448606Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448606
N1C=C(C(O)=[O:7])N=N1.CN(C(O[N:17]1[N:25]=[N:24][C:19]2[CH:20]=CC=N[C:18]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN([CH:39]([CH3:41])C)C(C)C.[C:42]1([C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)[CH:47]=[CH:46][C:45]([CH2:48][C@@H:49]([NH:58]C(OC(C)(C)C)=O)[CH2:50][C@:51]([CH2:56][OH:57])([CH3:55])[C:52]([OH:54])=[O:53])=[CH:44][CH:43]=1.Cl>CN(C=O)C.CCO.O1CCOCC1>[CH2:39]([O:54][C:52](=[O:53])[C@@:51]([CH2:56][OH:57])([CH3:55])[CH2:50][C@H:49]([NH:58][C:20]([C:19]1[NH:24][N:25]=[N:17][CH:18]=1)=[O:7])[CH2:48][C:45]1[CH:46]=[CH:47][C:42]([C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)=[CH:43][CH:44]=1)[CH3:41]

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 1401204-Carboxy-1,2,3-triazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68181022(2S,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-2-methyl-pentanoic acid

Produkt 1

HCID 178471713HCID 178471713, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

1,2,3-Triazole-4-carboxylic acid (11.5 mg, 102 nmol, 1.2 eq.) and HATU (38.6 mg, 102 nmol, 1.2 eq.) were dissolved in DMF (0.9 mL) and stirred at room temperature for 5 minutes. DIPEA (29.5 μL, 2.0 eq.) was added to yield the activated acid. (2S,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-2-methyl-pentanoic acid (35 mg, 85 μmol, 1.0 eq.) was dissolved in EtOH and 4 M of HCl in dioxane (423 μL) was added. The mixture was heated to 60° C. overnight, then concentrated to dryness and purified by reverse phase chromatography (5-60% MeCN in water over 18 minutes. The clean fractions were combined and dried under vacuum to dryness, then combined with the activated acid. After 20 minutes, the reaction was quenched with water and the product was dried under vacuum and purified by preparative HPLC to yield the title compound (4 mg, >95% purity. MS m/z [M+H]+ calc'd for C24H28N4O4, 437.21. found 437.3.

Aufarbeitung

  1. customto yield the activated acid
  2. temperatureThe mixture was heated to 60° C. overnight
  3. concentrationconcentrated to dryness
  4. custompurified by reverse phase chromatography (5-60% MeCN in water over 18 minutes
  5. customdried under vacuum to dryness
  6. waitAfter 20 minutes
  7. customthe reaction was quenched with water
  8. customthe product was dried under vacuum
  9. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-3eec78ea48ab4fcfba69b65b1267a2de
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481044B2

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