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

HRID 516438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 516438
[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 61,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-Hydroxy-1H-1,2,3-triazole-4-carboxylic acid (163 mg, 1.3 mmol) was combined with HCTU (523 mg, 1.3 mmol) and DMF, 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 (0.400 g, 1.26 mmol) were added, and the resulting mixture was stirred for 10 minutes. The mixture was evaporated under reduced pressure and purified (C18 column; 20-70% MeCN in water with 5% TFA) to yield the title compound (330 mg).

Aufarbeitung

  1. stirringthe resulting mixture was stirred for 10 minutes
  2. customThe mixture was evaporated under reduced pressure
  3. custompurified (C18 column; 20-70% MeCN in water with 5% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-5b52aae820ff4ea19b79d24f36e3a7b7
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108934B2

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