4-Carboxy-1,2,3-triazole → HCID 178459153, Verbindung

HRID 448605Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448605
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[N:3]=[N:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:33][C@H:34]([CH2:43][C:44]1[CH:49]=[CH:48][C:47]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[CH:46][CH:45]=1)[CH2:35][C@:36]([CH2:41][OH:42])([CH3:40])[C:37]([OH:39])=[O:38]>CCN(C(C)C)C(C)C.CN(C=O)C>[C:47]1([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[CH:46]=[CH:45][C:44]([CH2:43][C@@H:34]([NH:33][C:6]([C:4]2[NH:3][N:2]=[N:1][CH:5]=2)=[O:8])[CH2:35][C@:36]([CH2:41][OH:42])([CH3:40])[C:37]([OH:39])=[O:38])=[CH:49][CH:48]=1

Komponenten

6

Edukt 3

HCID 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 68181056(2S,4R)-4-Amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methylpentanoic acid

Produkt 1

HCID 178459153HCID 178459153, VerbindungAusbeute 30.699,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 81531DiisopropylethylamineLösungsmittel2×

Versuchsvorschrift

1,2,3-Triazole-4-carboxylic acid (130 mg, 1.2 mmol, 1.2 eq.) and HATU (400 mg, 1.1 mmol, 1.1 eq.) were dissolved in DIPEA (167 μL) and the resulting mixture was stirred for 5 minutes at room temperature in DMF (0.2 mL). DIPEA (3 eq.) and (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid (300 mg, 957 nmol, 1.0 eq.) dissolved in DMF (0.2 mL) was added, and the resulting mixture was stirred for 15 minutes. The reaction was quenched with AcOH and the product was purified by preparative HPLC then lyophilized to yield the title compound (120 mg, 95% purity). MS m/z [M+H]+ calc'd for C22H24N4O4, 409.18. found 409.4.

Aufarbeitung

  1. additionwas added
  2. customThe reaction was quenched with AcOH
  3. customthe product was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-f60e08b04d7a473eb13766b2684fcbb1
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481044B2

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