Lithium Hydroxide → (2S)-2-{3-[(1E)-3-(2-{[(3-ethylphenyl)amino]carbonyl}-1H-pyrrol-1-yl)prop-1-enyl]phenoxy}propanoic acid

HRID 1352875Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1352875
[CH2:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[N:13]([CH2:17]/[CH:18]=[CH:19]/[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C@@H:27]([CH3:36])[C:28](N4CCOCC4)=[O:29])[CH:21]=3)[CH:14]=[CH:15][CH:16]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)[CH3:2].[OH-:37].[Li+]>O1CCCC1.CO.O>[CH2:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[N:13]([CH2:17]/[CH:18]=[CH:19]/[C:20]3[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=3)[O:26][C@@H:27]([CH3:36])[C:28]([OH:37])=[O:29])[CH:14]=[CH:15][CH:16]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)[CH3:2]

Komponenten

6

Edukt 2

HCID 3939Lithium HydroxideHCID 69142288N-(3-ethylphenyl)-1-[(2E)-3-(3-{[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]oxy}phenyl)prop-2-enyl]-1H-pyrrole-2-carboxamide

Produkt 1

HCID 58863575(2S)-2-{3-[(1E)-3-(2-{[(3-ethylphenyl)amino]carbonyl}-1H-pyrrol-1-yl)prop-1-enyl]phenoxy}propanoic acidAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of N-(3-ethylphenyl)-1-[(2E)-3-(3-{[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]oxy}phenyl)prop-2-enyl]-1H-pyrrole-2-carboxamide (348 mg, 0.714 mmol) in tetrahydrofuran (4 ml), methanol (4 ml) and an aqueous 1N lithium hydroxide (6 ml) was stirred for 6 hours at 50° C. The reaction mixture was diluted with water, washed with diethyl ether. The aqueous layer was acidified with diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and an aqueous saturated sodium chloride solution and dried over magnesium sulfate. The solvent was removed to give the subject compound (264 mg, 88%).

Aufarbeitung

  1. washwashed with diethyl ether
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialan aqueous saturated sodium chloride solution and dried over magnesium sulfate
  5. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-619a76e4b76f4a168abe12753b2f43fa
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07220773B2

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