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Tetrahydrofuran → 2-Amino-4'-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone

HRID 275849
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 275849
O1CCCC1.CN(OC)[C:8](=[O:17])[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[NH2:16].[C:20]([O:24][C:25]([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32](Br)=[CH:31][CH:30]=1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C([Li])CCC>C(OC(=O)C)C.O.CCCCCC>[NH2:16][C:10]1[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=1[C:8]([C:32]1[CH:31]=[CH:30][C:29]([CH2:28][NH:27][C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])=[CH:34][CH:33]=1)=[O:17]
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Komponenten

8

Edukt 4

HCID 8028TetrahydrofuranHCID 12453839tert-butyl N-[(4-bromophenyl)methyl]carbamateHCID 222266052-amino-5-chloro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Produkt 1

HCID 183153642-Amino-4'-tert-butoxycarbonylaminomethyl-5-chlorobenzophenoneAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel
HCID 8058HexaneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A tetrahydrofuran (30 ml) solution of N-methyl-N-methyloxy-2-amino-5-chlorobenzamide (3.21 g) and N-tert-butoxycarbonyl-4-bromobenzylamine (2.86 g) was cooled to −78° C. To the solution kas gradually added dropwise a hexane solution of n-butyl lithium (1.6 mol/L) (31 ml). To the mixture were then added water (100 ml) and acetic acid ethyl ester (100 ml). The organic layer was washed with water and dried over anhydrous MgSO4. The solvent was then distilled off, and the residue was purified by means of a silica gel column chromatography. followed by crystallization. The crystals were collected to give 2-amino-4′-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone (0.9 g) as a pale yellow crystalline product.

Aufarbeitung

  1. washThe organic layer was washed with water
  2. dry with materialdried over anhydrous MgSO4
  3. distillationThe solvent was then distilled off
  4. customthe residue was purified by means of a silica gel column chromatography
  5. customfollowed by crystallization
  6. customThe crystals were collected

Quellen und Nachweise

ORD-Eintrag
ord-79d384d4b9734a568bbbe4fa09c91c97
Quelldatensatz
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06352982B1

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