Hydrochloric Acid → HCID 178447404, Verbindung

HRID 1590122Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1590122
C[O:2][C:3](=O)[C@H:4]([CH2:34][C:35]1[N:39]=[CH:38][NH:37][CH:36]=1)[NH:5][C:6](=[O:33])[C@H:7]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[NH:8][C:9](=[O:25])[C@H:10]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14].[BH4-].[Na+].Cl>O1CCCC1.CO>[OH:2][CH2:3][CH:4]([NH:5][C:6](=[O:33])[C@H:7]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[NH:8][C:9](=[O:25])[C@H:10]([CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:34][C:35]1[N:39]=[CH:38][NH:37][CH:36]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 178501418HCID 178501418, Verbindung

Produkt 1

HCID 178447404HCID 178447404, VerbindungAusbeute 68,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-Pivaloyl-L-phenylalanyl-L phenylalanyl-L-histidine methyl ester (1.90 g) is dissolved in tetrahydrofuran (12 ml), and a solution of sodium borohydride (0.20 g) in methanol (2.5 ml) is added dropwise thereto. The mixture is stirred at room temperature for four hours, and 5% hydrochloric acid (4 ml) is added to the mixture and then the solvent is distilled off. The residue is made alkaline with an aqueous sodium bicarbonate solution and then extracted with ethyl acetate. The extract is washed with an aqueous sodium chloride solution, dried, and concentrated to remove solvent. The residue is triturated with ethyl acetate to give 4-{2-hydroxymethyl-2-[N-(N-pivaloyl-L-phenylalanyl-L-phenylalanyl)amino]ethyl}imidazole (1.24 g) as white powder. Yield: 68.8%

Aufarbeitung

  1. distillationthe solvent is distilled off
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with an aqueous sodium chloride solution
  4. customdried
  5. concentrationconcentrated
  6. customto remove solvent
  7. customThe residue is triturated with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-6148a169ed8740b7b04230e0f02b26a3
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05202312

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