4-Iodoanisole → 2-tert-Butoxycarbonylamino-5-(4-methoxy-phenyl)-pentanoic acid methyl ester

HRID 1183029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1183029
[CH3:1][O:2][C:3](=[O:16])[CH:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH:6]=[CH2:7].B1C2CCCC1CCC2.I[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3](=[O:16])[CH:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:6][CH2:7][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1

Komponenten

6

Edukt 3

HCID 696764-IodoanisoleHCID 789669-Borabicyclo(3.3.1)nonaneHCID 10857232Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate

Produkt 1

HCID 669168592-tert-Butoxycarbonylamino-5-(4-methoxy-phenyl)-pentanoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a cooled (0° C.) mixture comprising 2-tert-butoxycarbonylamino-pent-4-enoic acid methyl ester (4.0 g, 17.46 mmol) in dry THF (60 mL) under an inert atmosphere of argon is added 9-BBN (70 mL of a 0.5 M solution in THF, 35.0 mmol). The reaction is stirred at RT for 2 h. To this mixture is added degassed DMF (50 mL) followed by an aqueous solution of potassium phosphate (12 mL of a 3 M aqueous solution, 36 mmol). 4-Iodoanisole (4.3 g, 18.8 mmol) is added immediately followed by PdCl2(dppf) (0.63 g, 0.86 mmol) and the mixture is stirred at RT overnight. The solvent is removed in vacuo and the crude residue is dissolved in EtOAc and filtered through Celite® (filter material). The filtrate is washed with saturated sodium hydrogen carbonate solution, water (×3), brine, and then dried (MgSO4) and concentrated in vacuo. Purification of the crude product by flash chromatography (SiO2, iso-hexane:EtOAc, 9:1) affords the title compound as a light brown oil.

Aufarbeitung

  1. additionTo this mixture is added
  2. customdegassed DMF (50 mL)
  3. stirringthe mixture is stirred at RT overnight
  4. customThe solvent is removed in vacuo
  5. dissolutionthe crude residue is dissolved in EtOAc
  6. filtrationfiltered through Celite® (filter material)
  7. washThe filtrate is washed with saturated sodium hydrogen carbonate solution, water (×3), brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customPurification of the crude product by flash chromatography (SiO2, iso-hexane:EtOAc, 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-212ed218cdb54b4eab7e02d77f076f07
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664228B2

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