Barium hydroxide, octahydrate → (S,E)-2-(2,6-dichlorobenzamido)-5-[4-(4-methoxytetrahydropyran-4-yl)-phenyl]pent-4-enoic acid

HRID 1752094

Reaktionsgleichung

Reaktionsgleichung von HRID 1752094
C[O:2][C:3](=[O:33])[C@@H:4]([NH:22][C:23](=[O:32])[C:24]1[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:31])[CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([C:14]2([O:20][CH3:21])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>C1COCC1.O>[Cl:31][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]([Cl:30])[C:24]=1[C:23]([NH:22][C@@H:4]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([C:14]2([O:20][CH3:21])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)[C:3]([OH:33])=[O:2])=[O:32]

Komponenten

5

Edukt 2

HCID 17749109Barium hydroxide, octahydrateHCID 57762529(S,E)-2-(2,6-dichlorobenzamido)-5-[4-(4-methoxytetrahydropyran-4-yl)-phenyl]pent-4-enoic acid methyl ester

Produkt 1

HCID 11533406(S,E)-2-(2,6-dichlorobenzamido)-5-[4-(4-methoxytetrahydropyran-4-yl)-phenyl]pent-4-enoic acidAusbeute 64,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In a mixed solvent of THF (250 ml) and water (125 ml), (S,E)-2-(2,6-dichlorobenzamido)-5-[4-(4-methoxytetrahydropyran-4-yl)-phenyl]pent-4-enoic acid methyl ester (9.80 g) was dissolved, and the resulting mixture was cooled to 0° C. Barium hydroxide octahydrate (3.14 g) was added thereto and the resulting mixture was stirred at 0° C. for 8 hours. The reaction solution was concentrated to remove THF, and water (150 ml) was added thereto, followed by washing the resulting mixture with ether. Aqueous layer was acidified by adding 1N hydrochloric acid in small portions thereto and extracted 3 times with ethyl acetate. Organic layers were washed with saturated brine and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by column chromatography (silica gel, eluent: chloroform/methanol=10/1). The obtained crude product was further purified by column chromatography (silica gel, eluent: cyclohexane/ethyl acetate=1/1→ethyl acetate) to obtain (S,E)-2-(2,6-dichlorobenzamido)-5-[4-(4-methoxytetrahydropyran-4-yl)-phenyl]pent-4-enoic acid (6.15 g).

Aufarbeitung

  1. concentrationThe reaction solution was concentrated
  2. customto remove THF, and water (150 ml)
  3. additionwas added
  4. washby washing the resulting mixture with ether
  5. additionby adding 1N hydrochloric acid in small portions
  6. extractionextracted 3 times with ethyl acetate
  7. washOrganic layers were washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customAfter removing anhydrous sodium sulfate
  10. filtrationby filtration
  11. concentrationthe filtrate was concentrated
  12. customThe residue was purified by column chromatography (silica gel, eluent: chloroform/methanol=10/1)
  13. customThe obtained crude product
  14. customwas further purified by column chromatography (silica gel, eluent: cyclohexane/ethyl acetate=1/1→ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-7d015e262b4541d1a628450748d8f32a
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09162988B2

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