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

HRID 1360084

반응식

HRID 1360084 반응식
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]

참가 물질

5

반응물 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

생성물 1

HCID 11533406(S,E)-2-(2,6-dichlorobenzamido)-5-[4-(4-methoxytetrahydropyran-4-yl)-phenyl]pent-4-enoic acid수율 64.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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 crudely purified product was further purified by column chromatography (silica gel, eluent:cyclohexane/ethyl acetate=ethyl acetate) to obtain (S,E)-2-(2,6-dichlorobenzamido)-5-[4-(4-methoxytetrahydropyran-4-yl)-phenyl]pent-4-enoic acid (6.15 g).

후처리

  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 crudely purified product
  14. customwas further purified by column chromatography (silica gel, eluent:cyclohexane/ethyl acetate=ethyl acetate)

출처 및 근거

ORD 기록
ord-488acb9e6bff47a1a7cbfcd11221e550
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879837B2

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