Tetrahydrofuran → N-(cholest-5-ene-3beta-oxycarbonyl)glycylglycine

HRID 465293

Reaktionsgleichung

Reaktionsgleichung von HRID 465293
C(=O)([O-])O.[Na+].O1CCCC1.[NH2:11][CH2:12][C:13]([NH:15][CH2:16][C:17]([OH:19])=[O:18])=[O:14].[CH3:20][C@@H:21]([C@@H:28]1[C@@:32]2([CH3:50])[CH2:33][CH2:34][CH:35]3[C@@:40]4([CH3:49])[CH2:41][CH2:42][CH:43]([O:45][C:46](Cl)=[O:47])[CH2:44][C:39]4=[CH:38][CH2:37][CH:36]3[CH:31]2[CH2:30][CH2:29]1)[CH2:22][CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26]>O>[CH3:27][CH:25]([CH2:24][CH2:23][CH2:22][C@H:21]([C@@H:28]1[C@:32]2([CH3:50])[C@H:31]([C@H:36]3[C@H:35]([CH2:34][CH2:33]2)[C@:40]2([CH3:49])[C:39]([CH2:44][C@@H:43]([O:45][C:46]([NH:11][CH2:12][C:13]([NH:15][CH2:16][C:17]([OH:19])=[O:18])=[O:14])=[O:47])[CH2:42][CH2:41]2)=[CH:38][CH2:37]3)[CH2:30][CH2:29]1)[CH3:20])[CH3:26]

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 11163GlycylglycineHCID 516892Sodium BicarbonateHCID 54236888C28H45ClO2

Produkt 1

HCID 131717552N-(cholest-5-ene-3beta-oxycarbonyl)glycylglycineAusbeute 80,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium hydrogencarbonate (0.168 g) and tetrahydrofuran (20 ml) were added to a suspension of glycylglycine (0.15 g) in water (20 ml). After tetrahydrofuran (20 ml) and cholesteryl chloroformate (0.898 g) were added to the resulting transparent solution at 0° C., the mixture was stirred for an hour. The reaction mixture was concentrated under reduced pressure and, methanl (10 ml) and chloroform (10 ml) were added to the residue. By filtration, the transparent solution was obtained. The solvent was distilled off to give crude crystals (0.98 g). The crude crystals were then purified by silica gel chromatography to give N-(cholest-5-ene-3β-oxycarbonyl)glycylglycine (0.5 g) as white powders.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure and, methanl (10 ml) and chloroform (10 ml)
  2. additionwere added to the residue
  3. filtrationBy filtration
  4. customthe transparent solution was obtained
  5. distillationThe solvent was distilled off
  6. customto give crude crystals (0.98 g)
  7. customThe crude crystals were then purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c01942f2ad344ee7b3deac1007c75775
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05152999

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