Tetrahydrofuran → 2-Amino-3-tert-butoxycarbonylaminomethyl-5-methyloxy-benzophenone

HRID 275860Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 275860
[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:6][N:7](OC)[C:8](=O)[C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[NH2:17].[C:21]([O:25]C(NCC1C=CC=C(Br)C=1)=O)([CH3:24])([CH3:23])[CH3:22].[CH2:37]([Li])[CH2:38][CH2:39]C.C(OCC)(=[O:44])C>O.CCCCCC>[NH2:17][C:10]1[C:9]([CH2:8][NH:7][C:6]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:44])=[CH:14][C:13]([O:15][CH3:16])=[CH:12][C:11]=1[C:5]([C:4]1[CH:39]=[CH:38][CH:37]=[CH:2][CH:3]=1)=[O:1]

Komponenten

8

Edukt 5

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 11033439tert-Butyl 3-bromobenzylcarbamateHCID 11514001Benzamide, 2-amino-N,5-dimethoxy-N-methyl-HCID 178418339Butyllithium

Produkt 1

HCID 183153612-Amino-3-tert-butoxycarbonylaminomethyl-5-methyloxy-benzophenone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A tetrahydrofuran (15 ml) solution of N-methyl-N-methyloxy-2-amino-5-methyloxy-benzamide (0.35 g) and N-tert-butoxycarbonyl-3-bromobenzylamine (0.48 g) was cooled to −70° C. To the solution was added dropwise, while stirring, a hexane solution of n-butyl lithium (1.6 mol/L) (6.2 ml) over 20 minutes. To the mixture were then added water (40 ml) and ethyl acetate (40 ml). The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography to give 2-amino-3-tert-butoxycarbonylaminomethyl-5-methyloxy-benzophenone as a yellow oily product (0.18 g).

Aufarbeitung

  1. additionTo the solution was added dropwise
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was purified by means of a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-aa58ea8698e54a2b8ea7bf3ca11587e8
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06352982B1

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