Sodium Bicarbonate → HCID 54522046, Verbindung

HRID 650800Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 650800
[CH3:1][NH:2][C:3](=[O:13])[C@@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:5].[C:14]([O:18][C:19](=[O:35])[NH:20][C@@H:21]([CH:33]=O)[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)([CH3:17])([CH3:16])[CH3:15].C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO.O.C(O)(=O)C>[C:14]([O:18][C:19](=[O:35])[NH:20][C@@H:21]([CH2:33][NH:5][C@@H:4]([C:3](=[O:13])[NH:2][CH3:1])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)([CH3:17])([CH3:15])[CH3:16]

Komponenten

8

Edukt 4

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 13689668N-Methyl-D-phenylalaninamideHCID 51356832HCID 51356832, Verbindung

Produkt 1

HCID 54522046HCID 54522046, VerbindungAusbeute 30,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

D-Phenylalanine-N-methyl amide (1.50 g, 8.35 mmol) and (1R)-1-formyl-2-(2-naphthyl)ethylcarbamic acid tert-butyl ester (2.50 g, 8.35 mmol) were dissolved in methanol (40 ml). Molsieves (3 Å, 30 g) and acetic acid (3 ml) were added and the mixture was cooled with ice and sodium cyanoborohydride (0.80 g, 12.5 mmol) was added. The mixture was stirred overnight at room temperature. Water (30 ml) and saturated aqueous sodium hydrogen carbonate (30 ml) were added and the mixture was extracted with methylene chloride (3×40 ml). The combined organic phases were dried (magnesium sulfate) and the solvent was removed in vacuo. The residue was chromatographed on silica (3×30 cm) using ethyl acetate/heptane (1:1) as eluent to afford 1.19 g of ((1R)-1-(((1R)-1-methylcarbamoyl-2-phenylethylamino)methyl)-2-(2-naphthyl)ethyl)carbamic acid tert butyl ester

Aufarbeitung

  1. additionwas added
  2. extractionthe mixture was extracted with methylene chloride (3×40 ml)
  3. dry with materialThe combined organic phases were dried (magnesium sulfate)
  4. customthe solvent was removed in vacuo
  5. customThe residue was chromatographed on silica (3×30 cm)

Quellen und Nachweise

ORD-Eintrag
ord-6fb5a01c9c2a4d86b2a301c87275b75d
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06274584B1

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