1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-2-(4-Fluoro-3,5-dimethyl-phenylamino)-hexanoic acid tert-butoxy-amide

HRID 885502Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 885502
[F:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][C@H:10]([CH2:14][CH2:15][CH2:16][CH3:17])[C:11]([OH:13])=O)=[CH:4][C:3]=1[CH3:18].[C:19]([O:23][NH2:24])([CH3:22])([CH3:21])[CH3:20].C1C=CC2N(O)N=NC=2C=1.C[N+]1(C)[C@H]2CC3C=CC(O)=C4O[C@H]5[C@@H](O)C=C[C@@H]2[C@]5(C=34)CC1.CCN=C=NCCCN(C)C>ClCCl.O>[C:19]([O:23][NH:24][C:11](=[O:13])[C@H:10]([NH:9][C:5]1[CH:4]=[C:3]([CH3:18])[C:2]([F:1])=[C:7]([CH3:8])[CH:6]=1)[CH2:14][CH2:15][CH2:16][CH3:17])([CH3:22])([CH3:21])[CH3:20]

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 61063N-MethylmorphineHCID 757711-HydroxybenzotriazoleHCID 2777907O-tert-butylhydroxylamineHCID 69189506(R)-2-(4-Fluoro-3,5-dimethyl-phenylamino)-hexanoic acid

Produkt 1

HCID 86667068(R)-2-(4-Fluoro-3,5-dimethyl-phenylamino)-hexanoic acid tert-butoxy-amideAusbeute 38,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of crude (R)-2-(4-fluoro-3,5-dimethyl-phenylamino)-hexanoic acid (ca. 6.0 mmol), O-tert-butyl-hydroxyamine (2.261 g, 18.0 mmol), HOBT (0.811 g, 6.0 mmol), and N-methyl morphine (3.036 g, 30.0 mmol) in 20 mL of dichloromethane, was added EDCI (1.725 g, 9.0 mmol). After stirring at room temperature under N2 for 44 h, the reaction mixture was diluted with 60 mL of water and extracted with dichloromethane (60 mL×3). The organic extracts were combined and dried over anhydrous Na2SO4 and the solvents removed under reduced pressure. The product was isolated by Flash chromatography (silica gel) eluting with 0-30% ethyl acetate/hexanes to give the title compound as a pale yellow semi-solid (0.747 g, 38% yield). LC-MS: tR=8.8 min; m/z 325 (M+H)+.

Aufarbeitung

  1. extractionextracted with dichloromethane (60 mL×3)
  2. dry with materialdried over anhydrous Na2SO4
  3. customthe solvents removed under reduced pressure
  4. customThe product was isolated by Flash chromatography (silica gel)
  5. washeluting with 0-30% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-1ff177eb7e8149a3a056da007a31c06c
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242174B2

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