Triethylamine → HCID 59253981, Verbindung

HRID 83817

Reaktionsgleichung

Reaktionsgleichung von HRID 83817
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1.C(N(CC)CC)C.[CH2:25]([O:32][CH2:33][C:34](Cl)=[O:35])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CC(C)=O>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:34](=[O:35])[CH2:33][O:32][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 177085Benzyloxyacetyl chlorideHCID 146502966-(4-Aminophenoxy)-hexanoic acid methyl ester

Produkt 1

HCID 59253981HCID 59253981, VerbindungAusbeute 22,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a mixture of 6-(4-aminophenoxy)-hexanoic acid methyl ester 17 (25 g, 105 mmol) and triethylamine (21.4 g, 211.6 mmol) in acetone (200 ml) at 0° C. was added drop-wise benzyloxy acetyl chloride (25 g, 135.5 mmol) followed by stirring at room temp. for 12 hrs. The solids were filtered off, acetone distilled off and water (100 ml) added. Crude 53 was extracted into chloroform, washed with 5% sodium bicarbonate solution (2×100 ml), then water (100 ml), dried over sodium sulphate and distilled. Crude 53 was purified by column chromatography on silica gel using benzene as eluant to get pure 53 (9 g, 22.2%), an off-white powder with a m.p. between 46-49° C.

Aufarbeitung

  1. filtrationThe solids were filtered off
  2. distillationacetone distilled off
  3. additionwater (100 ml) added
  4. extractionCrude 53 was extracted into chloroform
  5. washwashed with 5% sodium bicarbonate solution (2×100 ml)
  6. dry with materialwater (100 ml), dried over sodium sulphate
  7. distillationdistilled
  8. customCrude 53 was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f2bb647e4bac41068032e52858f6f640
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846845B2

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