Potassium Iodide → Ethyl 7-Bromo-3-(3-(tert.-butoxycarbonylamino)propoxy)-naphthalen-2-carboxylate

HRID 2187640Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2187640
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([OH:17])[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.[C:18]([O:22][C:23]([NH:25][CH2:26][CH2:27][CH2:28]Cl)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([O:17][CH2:28][CH2:27][CH2:26][NH:25][C:23]([O:22][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:24])[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 10932310N-Boc-3-ChloropropylamineHCID 18476207Ethyl 7-bromo-3-hydroxy-2-naphthoate

Produkt 1

HCID 18476258Ethyl 7-Bromo-3-(3-(tert.-butoxycarbonylamino)propoxy)-naphthalen-2-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 3.8 g (12.88 mmol) ethyl 7-bromo-3-hydroxynaphthalen-2-carboxylate, 3.0 g (15.5 mmol) 1-(tert.-butoxycarbonylamino)-3-chloropropane (prepared according to Helv. Chim. Acta 76 (1993), 1644), 2.0 g (14.5 mmol) potassium carbonate, and a catalytic amount of potassium iodide in 20 ml dry DMF was stirred at 90° C. for 6 h. It was poured into water, extracted three times with ethyl acetate, and the combined organic layers were washed three times with water, dried over sodium sulfate, and concentrated in vacuo. The intermediate was purified by chromatography on silica gel with toluene/acetone 9:1 to give 5.8 g (100%) of a yellow oil, which solidified rapidly upon standing.

Aufarbeitung

  1. extractionextracted three times with ethyl acetate
  2. washthe combined organic layers were washed three times with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe intermediate was purified by chromatography on silica gel with toluene/acetone 9:1

Quellen und Nachweise

ORD-Eintrag
ord-6b5b9054a9464b6a999f6674ec845ef5
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06410562B1

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