Diisopropylethylamine → (2R,4R)-5-(4-Bromophenyl)-2-hydroxy-4-[(1-hydroxy-1H-1,2,3-triazole-4-carbonyl)amino]pentanoic Acid Ethyl Ester

HRID 2273482Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2273482
[OH:1][N:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[N:4]=[N:3]1.CN(C(ON1N=NC2C=CC(=CC1=2)Cl)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH2:44]([O:46][C:47](=[O:61])[C@H:48]([OH:60])[CH2:49][C@H:50]([NH2:59])[CH2:51][C:52]1[CH:57]=[CH:56][C:55]([Br:58])=[CH:54][CH:53]=1)[CH3:45]>CN(C=O)C>[CH2:44]([O:46][C:47](=[O:61])[C@H:48]([OH:60])[CH2:49][C@H:50]([NH:59][C:7]([C:5]1[N:4]=[N:3][N:2]([OH:1])[CH:6]=1)=[O:9])[CH2:51][C:52]1[CH:53]=[CH:54][C:55]([Br:58])=[CH:56][CH:57]=1)[CH3:45]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 42624899O-(6-Chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphateHCID 534331041-Hydroxy-1H-1,2,3-triazole-4-carboxylic AcidHCID 67969401(2R,4R)-4-amino-5-(4-bromophenyl)-2-hydroxypentanoic acid ethyl ester

Produkt 1

HCID 67969558(2R,4R)-5-(4-Bromophenyl)-2-hydroxy-4-[(1-hydroxy-1H-1,2,3-triazole-4-carbonyl)amino]pentanoic Acid Ethyl EsterAusbeute 59,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-Hydroxy-1H-1,2,3-triazole-4-carboxylic acid (163 mg, 1.3 mmol),), HCTU (523 mg, 1.3 mmol), and DMF were combined and stirred for 5 minutes at room temperature. DIPEA (661 μL, 3.8 mmol) and (2R,4R)-4-amino-5-(4-bromophenyl)-2-hydroxypentanoic acid ethyl ester (4 mg, 1.3 mmol) were added and the resulting mixture was stirred for 10 minutes. The reaction mixture was evaporated under reduced pressure and purified (C18 column; 20-70% MeCN in water with 0.05% TFA) to yield the title compound (330 mg).

Aufarbeitung

  1. stirringthe resulting mixture was stirred for 10 minutes
  2. customThe reaction mixture was evaporated under reduced pressure
  3. custompurified (C18 column; 20-70% MeCN in water with 0.05% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-25a6d45e571549d9972bfe1a0d3e5f0e
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120747B2

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