Water → N-(tert-butoxycarbonyl)-O-(3-nitrobiphenyl-2-yl)-L-serine

HRID 1670430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1670430
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O.Br[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[C:19]=1[O:27][CH2:28][C@@H:29]([C:38]([OH:40])=[O:39])[NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]>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].O1CCOCC1>[C:34]([O:33][C:31]([NH:30][C@H:29]([C:38]([OH:40])=[O:39])[CH2:28][O:27][C:19]1[C:20]([N+:24]([O-:26])=[O:25])=[CH:21][CH:22]=[CH:23][C:18]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:32])([CH3:37])([CH3:36])[CH3:35]

Komponenten

7

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 67328353O-(2-bromo-6-nitrophenyl)-N-(tert-butoxycarbonyl)-L-serine

Produkt 1

HCID 67328913N-(tert-butoxycarbonyl)-O-(3-nitrobiphenyl-2-yl)-L-serine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

331 mg of phenylboronic acid (2.72 mmol), 50.3 mg of 1,1′-bis(diphenylphosphino)ferrocenepalladium chloride (C35H30Cl4FeP2Pd, MW 816.65, 0.025 mmol) and 3.22 g of caesium carbonate (9.87 mmol) are introduced into a 100 mL round-bottomed flask, with stirring and under an argon atmosphere, containing 16 mL of water, 5 mL of dioxane and 1 g of 34 (2.47 mmol). The medium is heated at 100° C., with stirring, for 1 h. The dioxane is concentrated and the aqueous phase is acidified to pH 2-3, extracted twice with 50 ml of AcOEt. The combined organic phases are dried over MgSO4, filtered and evaporated to dryness. The crude product is chromatographed on a silica cartridge (150 g, eluent CH2Cl2/MeOH, in an MeOH gradient: 1 to 5%). 500 mg of expected product 35 (yellow oil) are recovered.

Aufarbeitung

  1. stirringwith stirring, for 1 h
  2. concentrationThe dioxane is concentrated
  3. extractionextracted twice with 50 ml of AcOEt
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude product is chromatographed on a silica cartridge (150 g, eluent CH2Cl2/MeOH
  8. custom500 mg of expected product 35 (yellow oil) are recovered

Quellen und Nachweise

ORD-Eintrag
ord-bc11571423cb4dd4911ebdfe2f61ff3e
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994161B2

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