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Triethylamine → Ethyl 4-((R)-(4-fluorophenyl)((R)-1-methylethylsulfinamido)-methyl)phenyl(methyl)phosphinate

HRID 1525253
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1525253
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[NH:9][S@@:10]([C:12](C)([CH3:14])[CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH3:23][PH:24]([O-])([O-:28])[O:25][CH2:26][CH3:27].CCN(CC)CC>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]>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C@@H:8]([NH:9][S@@:10]([CH:12]([CH3:13])[CH3:14])=[O:11])[C:5]2[CH:6]=[CH:7][C:2]([P:24]([CH3:23])(=[O:28])[O:25][CH2:26][CH3:27])=[CH:3][CH:4]=2)=[CH:17][CH:18]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 89462272(R)-N-((R)-(4-bromophenyl)(4-fluorophenyl)methyl)-2-methylpropane-2-sulfinamide2×HCID 178476778HCID 178476778, Verbindung

Produkt 1

HCID 117702236Ethyl 4-((R)-(4-fluorophenyl)((R)-1-methylethylsulfinamido)-methyl)phenyl(methyl)phosphinate

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

To (R)—N—((R)-(4-bromophenyl)(4-fluorophenyl)methyl)-2-methylpropane-2-sulfinamide, 18-c, (10 g, 0.026 mol), ethyl methylphosphite (5.6 g, 0.052 mol) and Et3N (7.88 g, 0.078 mol) in THF (100 ml) was added PdCl2(dppf) (2.2 g). The mixture was allowed to stir overnight at reflux. The mixture was filtered and the filtrate was concentrated under vacuum. The residue was taken into dichloromethane and washed with brine. The organic layer was concentrated under vacuum and the residue was purified over silica gel (petroleum ether:ethyl acetate=1/1) to provide the product, 18-d, (6.9 g, 68%).

Aufarbeitung

  1. temperatureat reflux
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under vacuum
  4. washwashed with brine
  5. concentrationThe organic layer was concentrated under vacuum
  6. customthe residue was purified over silica gel (petroleum ether:ethyl acetate=1/1)
  7. customto provide the product, 18-d, (6.9 g, 68%)

Quellen und Nachweise

ORD-Eintrag
ord-1451bc4d111347e9ad69cee44fe7bd91
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09079930B2

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