Triethylamine → HCID 69848869, Verbindung

HRID 352185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 352185
[CH3:1][O:2][C:3](=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)Br.C(N(CC)CC)C.[NH:20]1[CH2:25][CH2:24][S:23][CH2:22][CH2:21]1>O1CCCC1>[CH3:1][O:2][C:3](=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[N:20]1[CH2:25][CH2:24][S:23][CH2:22][CH2:21]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 67164ThiomorpholineHCID 137806Benzeneacetic acid, alpha-bromo-, methyl ester

Produkt 1

HCID 69848869HCID 69848869, VerbindungAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of racemic α-bromophenylacetic acid methyl ester, 5.0 g (22.0 mmol) in 120 mL of tetrahydrofuran was added 3.4 mL (22.0 mmol) of triethylamine and 6.7 g (66.0 mmol) of thiomorpholine. The reaction mixture was refluxed for four hours, cooled to ambient temperature and concentrated to dryness. The residue was partitioned between 20% isopropanol/chloroform and water. The mixture was washed with saturated sodium bicarbonate, washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography using a methanol/chloroform gradient as eluent. A second purification was performed using chloroform as eluent and was concentrated to dryness to yield 5.36 g (97%) of the desired mixture of isomers as a yellow oil. MS (ion spray) 252.1 (M+).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for four hours
  2. concentrationconcentrated to dryness
  3. customThe residue was partitioned between 20% isopropanol/chloroform and water
  4. washThe mixture was washed with saturated sodium bicarbonate
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by chromatography
  10. customA second purification
  11. concentrationwas concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-5b333947eed948619e3d6d5cb274428b
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743794B2

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