Hydrochloric Acid → 2-[(4-{2-[Benzyl(hexyl)amino]-2-oxoethyl}-2-methoxyphenoxy)methyl]benzoic acid

HRID 2111993

Reaktionsgleichung

Reaktionsgleichung von HRID 2111993
[CH2:1]([N:8]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:9](=[O:31])[CH2:10][C:11]1[CH:28]=[CH:27][C:14]([O:15][CH2:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([O:21]C)=[O:20])=[C:13]([O:29][CH3:30])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+].Cl>C1COCC1.O>[CH2:1]([N:8]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:9](=[O:31])[CH2:10][C:11]1[CH:28]=[CH:27][C:14]([O:15][CH2:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([OH:21])=[O:20])=[C:13]([O:29][CH3:30])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68870229Methyl 2-[(4-{2-[benzyl(hexyl)amino]-2-oxoethyl}-2-methoxyphenoxy)methyl]benzoate

Produkt 1

HCID 104806922-[(4-{2-[Benzyl(hexyl)amino]-2-oxoethyl}-2-methoxyphenoxy)methyl]benzoic acidAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 2-[(4-{2-[benzyl(hexyl)amino]-2-oxoethyl}-2-methoxyphenoxy)methyl]benzoate (98 mg, 0.195 mmol) was dissolved in THF (2 ml). Lithium hydroxide (9.3 mg, 0.389 mmol) solved in water (1 ml) was added. The mixture was put in a microwave oven (Smith Synthesizer) at 150° C. for 7 minutes. It was then acidified with 1% hydrochloric acid, pH˜3, and extracted with ethyl acetate. The organic extract was washed with brine and dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE®) SI, 2 g/6 ml) using DCM and then MeOH/DCM (0.5:99.5, then 1:99) as eluant gave 43 mg the desired product, yield 45%.

Aufarbeitung

  1. additionwas added
  2. customThe mixture was put in a microwave oven
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-4d5607cd0b9e44cdb75db7a0be38af85
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07521461B2

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