Dichloromethane → HCID 66658923, Verbindung

HRID 420825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 420825
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]([CH3:24])[CH2:16][NH:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])=[CH:11][CH:10]=2)O1.[C:26]([C:28]1[CH:29]=[C:30]([CH:36]=[CH:37][C:38]=1OS(C(F)(F)F)(=O)=O)[C:31]([O:33][CH2:34][CH3:35])=[O:32])#[N:27].C(Cl)Cl.CC([O-])=O.[K+]>COCCOC.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].O.CCO>[C:26]([C:28]1[CH:29]=[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:36]=[CH:37][C:38]=1[C:9]1[CH:10]=[CH:11][C:12]([C@H:15]([CH3:24])[CH2:16][NH:17][S:18]([CH:21]([CH3:22])[CH3:23])(=[O:19])=[O:20])=[CH:13][CH:14]=1)#[N:27]

Komponenten

9

Edukt 4

HCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 59120696HCID 59120696, VerbindungHCID 87093775HCID 87093775, Verbindung

Produkt 1

HCID 66658923HCID 66658923, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Stir a solution of (2R)-propane-2-sulfonic acid {2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-amide (50 g, 136.2 mmol), Ethyl 3-Cyano-4-trifluoromethanesulfonyloxy-benzoate (40 g, 123.8 mmol), PdCl2(dppf).DCM (3.03 g, 3.71 mmol) and KOAc (36.43 g, 371.4 mmol) in DME:EtOH:H2O (200 mL/200 mL/200 mL) under nitrogen at 80° C. for 50 minutes. Pour the reaction mixture into ice-water and extract it with EtOAc. Wash the organic layer with water and saturated aq. sodium chloride solution, dry over MgSO4, filter and concentrate it in vacuo. Subject residue to silica gel chromatography eluting with hexane/EtOAc 4:1 to 3:1. Triturate the product in hexane, filter and dry, to yield 37.95 g of 1-(S)-Ethyl 2-Cyano-4′-[1-methyl-2-(propane-2-sulfonylamino)-ethyl]-biphenyl-4-carboxylate (74%). MS(ES): m/z=413.1 [M-H].

Aufarbeitung

  1. extractionextract it with EtOAc
  2. washWash the organic layer with water and saturated aq. sodium chloride solution
  3. dry with materialdry over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate it in vacuo
  6. washSubject residue to silica gel chromatography eluting with hexane/EtOAc 4:1 to 3:1
  7. customTriturate the product in hexane
  8. filtrationfilter
  9. customdry

Quellen und Nachweise

ORD-Eintrag
ord-dce90cacff3f4f2a981c1fc36d66642b
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097652B2

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