Triethylamine → 4-{2-[2-(3-But-3-enyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3-methyl-benzoic acid methyl ester

HRID 1755100Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1755100
C(N(CC)CC)C.[CH3:8][O:9][C:10](=[O:24])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][S:19](Cl)(=[O:21])=[O:20])=[C:13]([CH3:23])[CH:12]=1.[CH2:25]([O:29][C:30]1[CH:31]=[C:32]([C:40]2[NH:44][C:43](=[O:45])[C:42]3([CH2:50][CH2:49][NH:48][CH2:47][CH2:46]3)[N:41]=2)[CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[CH2:26][CH:27]=[CH2:28]>C(Cl)Cl>[CH3:8][O:9][C:10](=[O:24])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][S:19]([N:48]2[CH2:49][CH2:50][C:42]3([N:41]=[C:40]([C:32]4[CH:33]=[C:34]([C:36]([F:39])([F:37])[F:38])[CH:35]=[C:30]([O:29][CH2:25][CH2:26][CH:27]=[CH2:28])[CH:31]=4)[NH:44][C:43]3=[O:45])[CH2:46][CH2:47]2)(=[O:21])=[O:20])=[C:13]([CH3:23])[CH:12]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 668171362-(3-But-3-enyloxy-5-trifluoromethyl-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-oneHCID 866727954-(2-Chlorosulfonyl-ethyl)-3-methyl-benzoic acid methyl ester

Produkt 1

HCID 668187074-{2-[2-(3-But-3-enyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3-methyl-benzoic acid methyl esterAusbeute 94,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triethylamine (1.27 ml, 9.11 mmol) and 4-(2-chlorosulfonyl-ethyl)-3-methyl-benzoic acid methyl ester (1.01 g, 3.65 mmol) were added to a solution of 2-(3-but-3-enyloxy-5-trifluoromethyl-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (1.40 g, 3.83 mmol) in methylene chloride (35 ml) at 0° C. The mixture was stirred at room temperature for two hours, and then quenched with a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to give 4-{2-[2-(3-but-3-enyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3-methyl-benzoic acid methyl ester (2.10 g). This compound was used in the next reaction without further purification.

Aufarbeitung

  1. customquenched with a saturated aqueous ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7755b2209c6c48eabc92be2825724f02
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169254B2

Notizen zur Reaktion

Wird geladen…