Hydrochloric Acid → 3-{4-[1-(2-Formyl-4'-isopropyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-propionic acid

HRID 1160918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1160918
[CH3:1][O:2][C:3](=[O:42])[CH2:4][CH2:5][NH:6][C:7](=[O:41])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=3)=[C:22]([CH:35]3OCCC[O:36]3)[CH:21]=2)[CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:10][CH:9]=1.Cl.[OH-].[Na+]>C1COCC1>[CH3:1][O:2][C:3](=[O:42])[CH2:4][CH2:5][NH:6][C:7](=[O:41])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([CH:32]([CH3:33])[CH3:34])=[CH:28][CH:27]=3)=[C:22]([CH:35]=[O:36])[CH:21]=2)[CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:10][CH:9]=1.[CH:35]([C:22]1[CH:21]=[C:20]([O:19][CH:14]([C:11]2[CH:12]=[CH:13][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:42])=[O:2])=[O:41])=[CH:9][CH:10]=2)[CH2:15][CH:16]([CH3:17])[CH3:18])[CH:25]=[CH:24][C:23]=1[C:26]1[CH:31]=[CH:30][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=1)=[O:36]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 671535813-{4-[1-(2-[1,3]Dioxan-2-yl-4'-isopropyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-propionic acid methyl ester

Produkt 2

HCID 595181533-{4-[1-(2-Formyl-4'-isopropyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-propionic acidHCID 866159863-{4-[1-(2-Formyl-4'-isopropyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-propionic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-{4-[1-(2-[1,3]Dioxan-2-yl-4′-isopropyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-propionic acid methyl ester (570 mg) is taken into THF (10 ml), treated with 5N HCl for 5 h, neutralfied with 5N NaOH, extracted with ethyl acetate, dried over MgSO4 and concentrated. The residue is purified by column chromatography to afford 3-{4-[1-(2-formyl-4′-isopropyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-propionic acid methyl ester (36 mg) and 3-{4-[1-(2-formyl-4′-isopropyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-propionic acid (228 mg). MS (ES): 502.2 [M+H]+.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue is purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3e6f2cb4b6db4e18a0150f2e5661d971
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816557B2

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