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(S)-tert-butyl 3-(3-iodophenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate → (5)-Tert-butyl 3-(3-(but-3-enyl)phenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate

HRID 1471627
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1471627
I[C:2]1[CH:3]=[C:4]([CH2:8][C@H:9]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=1.[CH2:30]([Mg]Br)[CH2:31][CH:32]=[CH2:33]>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]>[CH2:33]([C:2]1[CH:3]=[C:4]([CH2:8][C@H:9]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:26])[CH3:27])[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=1)[CH2:32][CH:31]=[CH2:30]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 90289973(S)-tert-butyl 3-(3-iodophenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamateHCID 178418797HCID 178418797, Verbindung

Produkt 1

HCID 130272769(5)-Tert-butyl 3-(3-(but-3-enyl)phenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamateAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (5)-tert-butyl 3-(3-iodophenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate (510 mg, 1.0 mmol), Pd(dppf)Cl2 (10 mol %) in THF (5 ml) was added but-3-enylmagnesium bromide (8 ml, 4 mmol, 0.5 M in THF). The solution was then heated at reflux overnight. The solution was cooled down and quenched with ammonia chloride (aq) and filtered through celite. The filtrate was extracted with EtOAc (2×25 ml). The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was introduced to a silica gel loading column and purified by column chromatography (20-40% EtOAc/hexanes) to provide the desired product (270 mg, 0.62 mmol), 62%. MS (m/z) 439 [M+H]+. Intermediate I-1A was used in the synthesis of Example 4.

Aufarbeitung

  1. temperatureThe solution was then heated
  2. temperatureat reflux overnight
  3. temperatureThe solution was cooled down
  4. customquenched with ammonia chloride (aq)
  5. filtrationfiltered through celite
  6. extractionThe filtrate was extracted with EtOAc (2×25 ml)
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. additionThe crude product was introduced to a silica gel loading column
  11. custompurified by column chromatography (20-40% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f3af99928b1e41a1a076cfaccc586a83
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09012441B2

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