Lithium Hydroxide → 1-{3-[(tert-butoxycarbonyl)amino]propyl}-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-6-carboxylic acid

HRID 899919

Reaktionsgleichung

Reaktionsgleichung von HRID 899919
[OH-].[Li+].[C:3]([O:7][C:8]([NH:10][CH2:11][CH2:12][CH2:13][N:14]1[C:18]2[CH:19]=[C:20]([C:23]([O:25]C)=[O:24])[CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[NH:27][C:28]1[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>O1CCCC1.O>[C:3]([O:7][C:8]([NH:10][CH2:11][CH2:12][CH2:13][N:14]1[C:18]2[CH:19]=[C:20]([C:23]([OH:25])=[O:24])[CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[NH:27][C:28]1[CH:29]=[C:30]([O:38][CH3:39])[C:31]([O:36][CH3:37])=[C:32]([O:34][CH3:35])[CH:33]=1)=[O:9])([CH3:5])([CH3:4])[CH3:6]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 11962078methyl 1-{3-[(tert-butoxycarbonyl)amino]propyl}-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-6-carboxylate

Produkt 1

HCID 687922531-{3-[(tert-butoxycarbonyl)amino]propyl}-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-6-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium hydroxide (2.18 g, 6 eq) is added to a solution of methyl 1-{3-[(tert-butoxycarbonyl)amino]propyl}-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-6-carboxylate (4.4 g, 1 eq) in a mixture of tetrahydrofuran (40 ml) and water (30 ml). The mixture is heated under reflux for 18 hours then cooled down to ambient temperature and concentrated under reduced pressure at 40° C. Dichloromethane (150 ml) and water (100 ml) are added to the residue. The mixture is acidified by the addition of acetic acid to pH 5. After decantation and extractions, the combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. The solid obtained is washed with ethyl ether (3.95 g; 93%).

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 18 hours
  3. concentrationconcentrated under reduced pressure at 40° C
  4. additionDichloromethane (150 ml) and water (100 ml) are added to the residue
  5. additionThe mixture is acidified by the addition of acetic acid to pH 5
  6. extractionAfter decantation and extractions
  7. dry with materialthe combined organic phases are dried over sodium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customThe solid obtained
  10. washis washed with ethyl ether (3.95 g; 93%)

Quellen und Nachweise

ORD-Eintrag
ord-a29414aaaf8c49c7842c8da21507a65b
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07355052B2

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