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Lithium Hydroxide → 2-{[4-(2-Oxo-2-{[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]methyl}benzoic acid

HRID 2111971
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2111971
[O:1]=[C:2]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1)[CH2:3][C:4]1[CH:21]=[CH:20][C:7]([O:8][CH2:9][C:10]2[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=2[C:12]([O:14]C)=[O:13])=[CH:6][CH:5]=1.[OH-].[Li+]>C1COCC1.O>[O:1]=[C:2]([NH:22][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:28][CH:29]=1)[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]2[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=2[C:12]([OH:14])=[O:13])=[CH:20][CH:21]=1
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Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 68869576Methyl 2-{[4-(2-oxo-2-{[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]methyl}-benzoate

Produkt 1

HCID 98246612-{[4-(2-Oxo-2-{[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]methyl}benzoic acidAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

Methyl 2-{[4-(2-oxo-2-{[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]methyl}-benzoate (71 mg, 0.155 mmol) in THF (1.5 ml) was cooled in an ice-bath. Lithium hydroxide (7.5 mg, 0.310 mmol) in water (1.5 ml) was dropped in. The cooling-bath was then removed and the mixture was stirred overnight. HPLC showed that the reaction was not complete. More lithium hydroxide (0.2M, 0.5 ml) was added. The reaction mixture was stirred for 4 days more. It was then evaporated in vacuum to remove THF. The residue was acidified with 1% hydrochloric acid, pH=3-4, and then extracted with ethyl acetate. The organic phase was dried with magnesium sulphate and evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 2 g/6 ml) using DCM, MeOH/DCM (0.5:99.5, then 1:99, and then 2:98) as eluant gave 39 mg white solid product, yield 57%.

Aufarbeitung

  1. customThe cooling-bath was then removed
  2. additionMore lithium hydroxide (0.2M, 0.5 ml) was added
  3. stirringThe reaction mixture was stirred for 4 days more
  4. customIt was then evaporated in vacuum
  5. customto remove THF
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic phase was dried with magnesium sulphate
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e2f3f06dab3e43ff81ad5f19304d604f
Quelldatensatz
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07521461B2

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