Sodium Hydroxide → Ethoxy[4-(2-hydroxy-4-methylphenyl)-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]acetic acid

HRID 63950Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 63950
C([O:3][C:4](=[O:31])[CH:5]([O:28][CH2:29][CH3:30])[C:6]1[C:7]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:21]=2[OH:27])=[C:8]2[C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=3[S:13][C:9]2=[N:10][C:11]=1[CH3:12])C.[OH-].[Na+]>C(O)C.O1CCCC1>[CH2:29]([O:28][CH:5]([C:6]1[C:7]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:21]=2[OH:27])=[C:8]2[C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=3[S:13][C:9]2=[N:10][C:11]=1[CH3:12])[C:4]([OH:31])=[O:3])[CH3:30]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 136372354Ethoxy-[4-(2-hydroxy-4-methyl-phenyl)-2-methyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl]-acetic acid ethyl ester

Produkt 1

HCID 136372353Ethoxy[4-(2-hydroxy-4-methylphenyl)-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]acetic acidAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred solution of Ethoxy-[4-(2-hydroxy-4-methyl-phenyl)-2-methyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl]-acetic acid ethyl ester (20 mg, 45 μmols) in ethanol (1 mL) and tetrahydrofuran (1 mL) was added the sodium hydroxide (2N aqueous, 0.5 mL, 20 eq) and the reaction was stirred at 60° C. for 5 hours. The reaction was concentrated in vacuo until all organic solvents had been removed, the aqueous residue was then acidified with hydrochloric acid (2N aqueous) to pH 2. A pale yellow solid, 4 mg (16% yield) was filtered off and analysed and found to contain ethoxy-[4-(2-hydroxy-4-methyl-phenyl)-2-methyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl]-acetic acid. LC-MS (12 min acidic) 5.04 mins 47-43% pure by UV, ES+/APCI+ 412, ES−/APCI− 410; 5.80 mins 12-13% pure by UV, ES+/APCI+ 412, ES−/APCI− 410.

Aufarbeitung

  1. concentrationThe reaction was concentrated in vacuo until all organic solvents
  2. customhad been removed
  3. filtrationA pale yellow solid, 4 mg (16% yield) was filtered off
  4. customLC-MS (12 min acidic) 5.04 mins 47-43%
  5. custom5.80 mins 12-13%

Quellen und Nachweise

ORD-Eintrag
ord-886aa54941de4666b10e4324429c56ad
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447116B2

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