Sodium Hydroxide → 3-{4-[1-(4'-tert-Butyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-2(R)-hydroxy-propionic acid

HRID 1914318Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1914318
C[O:2][C:3](=[O:38])[C@H:4]([OH:37])[CH2:5][NH:6][C:7](=[O:36])[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]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)[CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:10][CH:9]=1.[OH-].[Na+]>CO>[C:32]([C:29]1[CH:28]=[CH:27][C:26]([C:23]2[CH:24]=[CH:25][C:20]([O:19][CH:14]([C:11]3[CH:10]=[CH:9][C:8]([C:7]([NH:6][CH2:5][C@@H:4]([OH:37])[C:3]([OH:38])=[O:2])=[O:36])=[CH:13][CH:12]=3)[CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:21][CH:22]=2)=[CH:31][CH:30]=1)([CH3:34])([CH3:35])[CH3:33]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 671535413-{4-[1-(4'-tert-butyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-2(R)-hydroxy-propionic acid methyl ester

Produkt 1

HCID 595180383-{4-[1-(4'-tert-Butyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-2(R)-hydroxy-propionic acidAusbeute 104,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of 3-{4-[1-(4′-tert-butyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-2(R)-hydroxy-propionic acid methyl ester (60 mg, 0.12 mmol) in methanol (2 mL) is added sodium hydroxide (5 N aqueous, 0.5 mL) and stirred for 5 h. The reaction mixture is concentrated and acidified by 5 N HCl (0.5 mL), extracted with ethyl acetate. Combined organic layers are washed with water and brine, dried over sodium sulfate. Concentration gives the title compound (63 mg). MS (ES): 504.3 [M+H]+.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated
  2. extractionextracted with ethyl acetate
  3. washCombined organic layers are washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentration

Quellen und Nachweise

ORD-Eintrag
ord-1e756826dc2a4111bde818c8c7b14a7a
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609892B2

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