Ammonium → (S)-2-Amino-3-[4-(tert-butoxy)phenyl]propanamide

HRID 895161

Reaktionsgleichung

Reaktionsgleichung von HRID 895161
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 15024317(S)-2-Amino-3-[4-(tert-butoxy)phenyl]propanamideAusbeute 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-b15450ccefdb4851b3300913d415f364
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06914069B2

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