Isobutyryl chloride → [5-(Benzyl-isobutyryl-amino)-2-propyl-benzoimidazol-1-yl]-acetic acid tert-butyl ester

HRID 15580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 15580
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[C:7]([O:11][C:12](=[O:34])[CH2:13][N:14]1[C:18]2[CH:19]=[CH:20][C:21]([NH:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:22][C:17]=2[N:16]=[C:15]1[CH2:31][CH2:32][CH3:33])([CH3:10])([CH3:9])[CH3:8].CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl.Cl>[C:7]([O:11][C:12](=[O:34])[CH2:13][N:14]1[C:18]2[CH:19]=[CH:20][C:21]([N:23]([CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])=[CH:22][C:17]=2[N:16]=[C:15]1[CH2:31][CH2:32][CH3:33])([CH3:10])([CH3:9])[CH3:8]

Komponenten

7

Edukt 3

HCID 62325Isobutyryl chlorideHCID 81531DiisopropylethylamineHCID 67200053(5-Benzylamino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester

Produkt 1

HCID 67200174[5-(Benzyl-isobutyryl-amino)-2-propyl-benzoimidazol-1-yl]-acetic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Isobutyryl chloride (38 μL, 0.36 mmol) was added to a solution of (5-benzylamino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester (45 mg, 0.12 mmol), DIEA (41 μL, 0.24 mmol) and DMAP (15 mg, 0.12 mmol) in CH2Cl2 (1 mL), and stirred overnight at room temperature. The reaction solution was diluted with aqueous HCl (1.0 M) and filtered through an Extrelut column. The Extrelut column was washed with CH2Cl2, and the filtrate was concentrated to afford the subtitle compound that was used without further purification. MS calculated for C27H35N3O3+H: 450, observed: 450.

Aufarbeitung

  1. filtrationfiltered through an Extrelut column
  2. washThe Extrelut column was washed with CH2Cl2
  3. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-6214346e4a9842cb87e4219a874af32a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732618B2

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