Hexane → 2-Amino-3'-(2-tert-butoxycarbonylaminoethyl)-5-chloro-benzophenone

HRID 275867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 275867
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13](Br)[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(OC)[C:20](=[O:29])[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[NH2:28].CCCCCC.C([Li])CCC>O1CCCC1.C(OCC)(=O)C.O>[NH2:28][C:22]1[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:21]=1[C:20]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:12]=1)=[O:29]

Komponenten

8

Edukt 4

HCID 8058HexaneHCID 18315328Tert-butyl 3-bromophenethylcarbamateHCID 222266052-amino-5-chloro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Produkt 1

HCID 183153892-Amino-3'-(2-tert-butoxycarbonylaminoethyl)-5-chloro-benzophenoneAusbeute 70,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of N-tert-butoxycarbonyl-3-bromophenethylamine (1.7 g) and N-methyl-N-methyloxy-2-amino-5-chloro-benzamide (1.9 g) in tetrahydrofuran (50 ml) was cooled to -70° C. To the solution was added dropwise, while stirring, a hexane solution of n-butyl lithium (1.6 mol/L) (18 ml). To the reaction mixture were added water (100 ml) and ethyl acetate (80 ml). The mixture was shaken. The organic layer was separated, which was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by means of a silica gel column chromatography to give 2-amino-3′-(2-tert-butoxycarbonylaminoethyl)-5-chloro-benzophenone (1.5 g) as a yellow crystalline product. m.p.: 128-129° C.

Aufarbeitung

  1. additionTo the solution was added dropwise
  2. stirringThe mixture was shaken
  3. customThe organic layer was separated
  4. washwhich was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by means of a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-52e078ed5ef54f3082b3b1bda7d562bb
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06352982B1

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