Sodium Hydroxide → HCID 44599428, Verbindung

HRID 1021563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1021563
[CH3:1][O:2][C:3]1[CH:36]=[C:35]([CH:37]2[CH2:39][CH2:38]2)[CH:34]=[CH:33][C:4]=1[CH2:5][CH2:6][NH:7][C:8]([C:10]1[CH:32]=[CH:31][C:13]([O:14][C:15]2[CH:24]=[C:23]3[C:18]([CH:19]([C:25]([O:27]CC)=[O:26])[CH2:20][CH2:21][O:22]3)=[CH:17][C:16]=2[Cl:30])=[CH:12][CH:11]=1)=[O:9].[OH-].[Na+]>C1COCC1.C(O)C.CCOC(C)=O.Cl>[Cl:30][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:15]=1[O:14][C:13]1[CH:31]=[CH:32][C:10]([C:8](=[O:9])[NH:7][CH2:6][CH2:5][C:4]3[CH:33]=[CH:34][C:35]([CH:37]4[CH2:39][CH2:38]4)=[CH:36][C:3]=3[O:2][CH3:1])=[CH:11][CH:12]=1)[O:22][CH2:21][CH2:20][CH:19]2[C:25]([OH:27])=[O:26]

Komponenten

7

Edukt 2

HCID 14798Sodium HydroxideHCID 67081068HCID 67081068, Verbindung

Produkt 1

HCID 44599428HCID 44599428, VerbindungAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of ethyl 7-(4-(2-methoxy-4-cyclopropylphenethylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylate (0.07 g; 0.133 mmol) in a mixture of 1.2 mL THF and 0.6 mL ethanol at ambient temperature was added 0.53 mL of 1M aqueous NaOH. The resulting slightly cloudy mixture was vigorously stirred at ambient temperature. After 1 hour the reaction mixture was diluted with 6 mL EtOAc and 3 mL of 1M aqueous HCl, then transferred to a separatory funnel. After shaking, the organic layer was washed with 2 mL brine, then dried over sodium sulfate and evaporated to give 62 mg of 6-chloro-7-(4-(4-cyclopropyl-2-methoxyphenethylcarbamoyl)phenoxy)chroman-4-carboxylic acid as a colorless oil. MS (apci, pos) m/z=523.

Aufarbeitung

  1. customtransferred to a separatory funnel
  2. stirringAfter shaking
  3. washthe organic layer was washed with 2 mL brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-62b31cd8f93447c693139dd023cc63ef
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716498B2

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