Triethylamine → (S)-2-({1-[2-(4'-tert-butylbiphenyl-3-yl)-9-hydroxy-3H-naphtho[1,2-d]imidazol-7-yl]-methanoyl}-amino)-3-phenylpropionic Acid

HRID 25324Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 25324
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[NH:18][C:19]4[CH:29]=[CH:28][C:27]5[C:22](=[C:23]([OH:33])[CH:24]=[C:25]([C:30](O)=[O:31])[CH:26]=5)[C:20]=4[N:21]=3)[CH:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.C([O:39][C:40](=[O:50])[C@H:41]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[NH2:42])(C)(C)C.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>CN(C)C=O.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[NH:18][C:19]4[CH:29]=[CH:28][C:27]5[C:22](=[C:23]([OH:33])[CH:24]=[C:25]([C:30]([NH:42][C@@H:41]([CH2:43][C:44]6[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=6)[C:40]([OH:50])=[O:39])=[O:31])[CH:26]=5)[C:20]=4[N:21]=3)[CH:12]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 103429852-(4'-tert-butylbiphenyl-3-yl)-9-hydroxy-3H-naphtho[1,2-d]imidazole-7-carboxylic acidHCID 11459563L-Phenylalanine, 1,1-dimethylethyl ester, hydrochloride (1:1)

Produkt 1

HCID 69557908(S)-2-({1-[2-(4'-tert-butylbiphenyl-3-yl)-9-hydroxy-3H-naphtho[1,2-d]imidazol-7-yl]-methanoyl}-amino)-3-phenylpropionic Acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To the 2-(4′-tert-butylbiphenyl-3-yl)-9-hydroxy-3H-naphtho[1,2-d]imidazole-7-carboxylic acid (0.047 g, 0.1 mmol) in dimethylformamide (0.5 mL)at room temperature was added phenylalanine tert butyl ester hydrochloride (0.11 mmol). A cocktail solution of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.021 g, 0.11 mmol), triethylamine (0.3 mmol) in DMF (0.5 mL) was added and the reaction was agitated at room temperature for 18 hours. 1 ml water was added to the reaction mixture resulting in the formation of a tan precipitate. the mixture was filtered and allowed to dry. The solid mass was transferred into vial and dissolved in 1 ml of 90% trifluoroacetic acid. The solutions were agitated for 6 hrs then concentrated under reduced pressure. The residures were taked up in DMSO and subjected to Gilson HPLC purification. The title compound was abtained as solid.(0.016 g, 28%). MS(ES) m/z 584 [M+H].

Aufarbeitung

  1. customresulting in the formation of a tan precipitate
  2. filtrationthe mixture was filtered
  3. customto dry
  4. dissolutiondissolved in 1 ml of 90% trifluoroacetic acid
  5. stirringThe solutions were agitated for 6 hrs
  6. concentrationthen concentrated under reduced pressure
  7. customsubjected to Gilson HPLC purification

Quellen und Nachweise

ORD-Eintrag
ord-819c30fcaec045999eae03b3457aa01c
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858630B2

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