Dichloromethane → HCID 54341699, Verbindung

HRID 361458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 361458
[CH2:1]([O:5][C:6]([N:8]([C:26]1[C:31]([O:32][CH3:33])=[N:30][C:29]([CH3:34])=[CH:28][N:27]=1)[S:9]([C:12]1[C:13]([C:18]2[CH:23]=[CH:22][C:21]([CH:24]=O)=[CH:20][CH:19]=2)=[N:14][CH:15]=[CH:16][CH:17]=1)(=[O:11])=[O:10])=[O:7])[CH:2]([CH3:4])[CH3:3].[Br-].[C:36]([CH2:39][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:38])=[O:37].[OH-].[Na+].[CH2:61](Cl)Cl>O>[CH2:1]([O:5][C:6]([N:8]([C:26]1[C:31]([O:32][CH3:33])=[N:30][C:29]([CH3:34])=[CH:28][N:27]=1)[S:9]([C:12]1[C:13]([C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[CH:39][C:36]([O:38][CH3:61])=[O:37])=[CH:20][CH:19]=2)=[N:14][CH:15]=[CH:16][CH:17]=1)(=[O:10])=[O:11])=[O:7])[CH:2]([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 21186316N-isobutoxycarbonyl-2-(4-formylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamideHCID 21186329Carboxymethyl triphenylphosphonium bromide

Produkt 1

HCID 54341699HCID 54341699, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

N-isobutoxycarbonyl-2-(4-formylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (500 mg) was added to carboxymethyl triphenylphosphonium bromide (429 mg) in a mixture of saturated aqueous sodium hydroxide (1.25 ml) and methylene chloride (4 ml) and stirred vigorously at ambient temperature for 1.5 hours. Water (20 ml) was added and the mixture extracted with dichloromethane (2×20 ml). The combined organic extracts were, washed with water (5 ml), dried (MgSO4) and evaporated. The residue was purified by chromatography on a Mega Bond Elut column, eluting with a gradient of 0-30% ethyl acetate in hexane. Fractions containing the product were combined, evaporated and the residue was triturated with diethyl ether/isohexane (1:1 v/v) and filtered to give N-isobutoxycarbonyl-2-[4-(2-[methoxycarbonyl]vinyl)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (366 mg), m.p 155°-156° C.; 1H NMR (CDCl3): 0.65 (d, 6 H), 1.7 (septet, 1 H), 2.5 (s, 3 H), 3.82 (s, 3 H), 3.85 (d, 2 H), 3.98 (s, 3 H), 6.48 (d, 1 H), 7.4-7.8 (m , 7 H), 7.9 (s, 1 H), 8.86 (dd, 1 H), 8.98 (dd, 1 H).

Aufarbeitung

  1. extractionthe mixture extracted with dichloromethane (2×20 ml)
  2. washwashed with water (5 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by chromatography on a Mega Bond Elut column
  6. washeluting with a gradient of 0-30% ethyl acetate in hexane
  7. additionFractions containing the product
  8. customevaporated
  9. customthe residue was triturated with diethyl ether/isohexane (1:1 v/v)
  10. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-15616f2e13284c47bd981b1f37988e7a
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866568

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