Ammonium → HCID 15024317, Verbindung

HRID 272790

Reaktionsgleichung

Reaktionsgleichung von HRID 272790
C([NH:18][C@H:19]([C:32]([OH:34])=O)[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:23][CH:22]=1)(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.[NH4+].C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C.[N:51]1C=CC=CC=1>O1CCOCC1.C(OCC)(=O)C.ClCCl.C(NCC)C>[C:28]([O:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][C@@H:19]([C:32]([NH2:51])=[O:34])[NH2:18])=[CH:22][CH:23]=1)([CH3:31])([CH3:30])[CH3:29]

Komponenten

9

Edukt 4

HCID 223AmmoniumHCID 1049PyridineHCID 90495Di-tert-butyl dicarbonateHCID 10895791Fmoc-L-Tyr(tBu)-OH

Produkt 1

HCID 15024317HCID 15024317, VerbindungAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6344DichloromethaneLösungsmittelHCID 8021DiethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

N-Fmoc-O-tert-butyl-tyrosine (3.27 g, 7.12 mmol) was dissolved in dioxane (15 mL). Ammonium hydrogenocarbonate (732 mg, 9.26 mmol), di-tert-butyl-dicarbonate (2.02 g, 9.26 mmol) and pyridine (0.4 mL) were added and the mixture was stirred under nitrogen atmosphere at room temperature for 12 h. It was then diluted with ethyl acetate and the organic phase was washed with brine (2×), 5% sulfuric acid (1×) and brine again. It was dried over magnesium sulfate and concentrated. The crude thus obtained (3.17 g) was dissolved in dichloromethane (50 mL) and diethylamine (10 mL). The mixture was stirred at room temperature for 12 h, concentrated under reduced pressure and purified by flash chromatography with DCM/MeOH/NH4OH (95/5/1 then 90/10/1) to give 1.37 g of the desired compound (yield=81%).

Aufarbeitung

  1. washthe organic phase was washed with brine (2×), 5% sulfuric acid (1×) and brine again
  2. dry with materialIt was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe crude thus obtained (3.17 g)
  5. stirringThe mixture was stirred at room temperature for 12 h
  6. concentrationconcentrated under reduced pressure
  7. custompurified by flash chromatography with DCM/MeOH/NH4OH (95/5/1

Quellen und Nachweise

ORD-Eintrag
ord-b3ee7894533f4b548def05bd37831a88
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456201B2

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