Phenacylamine → (s)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-n-(2-oxo-2-phenyl-ethyl)-3-phenyl-propionamide

HRID 1524858Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1524858
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([N:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:13]2=[O:14])[C:9]([OH:11])=O)=[CH:3][CH:2]=1.[NH2:23][CH2:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:26].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>N1C=CC=CC=1>[O:14]=[C:13]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21](=[O:22])[N:12]1[C@@H:8]([CH2:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)[C:9]([NH:23][CH2:24][C:25](=[O:26])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:11]

Komponenten

5

Edukt 3

HCID 11952PhenacylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 334207(2S)-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-3-phenylpropanoic acid

Produkt 1

HCID 66674794(s)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-n-(2-oxo-2-phenyl-ethyl)-3-phenyl-propionamideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

N-Phthaloyl-L-phenylalanine (290 mg, 1 mmol) and 2-aminoacetophenone (171 mg, 1 mmol) were dissolved in 10 mL of pyridine. Bop reagent (470 mg, 1.1 mmol) was added The mixture was stirred at rt under N2 for 12 h. The solvent was removed. The residue was dissolved in EtOAc and washed with water and sat. NaHCO3. The organic layer was dried over Na2SO4, filtered, and concentrated to yield 412 mg of the product (100% yield). MS 413.2 (M+H)+.

Aufarbeitung

  1. customThe solvent was removed
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with water and sat. NaHCO3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5462f1e45a1944999ce18cfd03fc8b28
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079860B2

Notizen zur Reaktion

Wird geladen…