Potassium Carbonate → N-Isoamyl-N-(6-hydroxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester

HRID 77321

Reaktionsgleichung

Reaktionsgleichung von HRID 77321
[C:1]([O:5][C:6](=[O:34])[C@@H:7]([CH:31]([CH3:33])[CH3:32])[N:8]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22]C(=O)C)[CH:18]=2)[CH:13]=1)(=[O:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[C:1]([O:5][C:6](=[O:34])[C@@H:7]([CH:31]([CH3:33])[CH3:32])[N:8]([CH2:26][CH2:27][CH:28]([CH3:29])[CH3:30])[S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([OH:22])[CH:18]=2)[CH:13]=1)(=[O:11])=[O:10])([CH3:3])([CH3:4])[CH3:2]

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 67155272N-isoamyl-N-(6-acetoxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester

Produkt 1

HCID 67155390N-Isoamyl-N-(6-hydroxy naphthalene-2-sulfonyl)-D-valine tert-butyl esterAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

To a solution of N-isoamyl-N-(6-acetoxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester (0.75 g, 1.53 mmol) in ethanol-water (35 mL-15 mL) is added potassium carbonate (0.422 g, 3.05 mmol), and the reaction is heated to reflux for 16 h. The solvents are removed in vacuo, and the residue is redissolved in water and extracted three times with dichloromethane. The combined organic extracts are washed with sodium bicarbonate and brine, dried over sodium sulfate, and concentrated in vacuo. The crude product is purified by column chromatography (10% hexanes-ethyl acetate) to afford the title compound as a yellow oil (0.58 g, 85% yield).

Aufarbeitung

  1. temperaturethe reaction is heated
  2. temperatureto reflux for 16 h
  3. customThe solvents are removed in vacuo
  4. dissolutionthe residue is redissolved in water
  5. extractionextracted three times with dichloromethane
  6. washThe combined organic extracts are washed with sodium bicarbonate and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe crude product is purified by column chromatography (10% hexanes-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-7a774f54f8724fa78ecf6c8d08696d59
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841291B2

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