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Lithium hydroxide, monohydrate → 3-(2-Carboxy-1-cyclohexyl-ethylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester

HRID 579194
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 579194
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:8][C:9]=1[NH:10][CH:11]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH2:12][C:13]([O:15]CC)=[O:14])=[O:4].O[Li].O>C1COCC1.CCO.O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:8][C:9]=1[NH:10][CH:11]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH2:12][C:13]([OH:15])=[O:14])=[O:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 666841133-(1-Cyclohexyl-2-ethoxycarbonyl-ethylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester

Produkt 1

HCID 666846033-(2-Carboxy-1-cyclohexyl-ethylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962
Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a solution of 3-(1-cyclohexyl-2-ethoxycarbonyl-ethylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester (300 mg, 0.72 mmol, 1.0 equiv) in THF (2.0 mL), EtOH (1.0 mL) and water (2.0 mL) was added LiOH.H2O (152 mg, 3.6 mmol, 5.0 equiv). The mixture was stirred at 55° C. for 20 minutes. The organic solvent was then evaporated. To the resulting solution was added 3.0 N HCl aq. solution until pH=5˜6. The solid was then collected by filtration and washed with water. The filtrate was extracted with EtOAc and the organic layer was washed with sat. NaHCO3 aq. solution, brine, dried over Na2SO4, and concentrated in vacuo. The crude material was continued to the next step with no further purification.

Aufarbeitung

  1. customThe organic solvent was then evaporated
  2. additionTo the resulting solution was added 3.0 N HCl aq. solution until pH=5˜6
  3. filtrationThe solid was then collected by filtration
  4. washwashed with water
  5. extractionThe filtrate was extracted with EtOAc
  6. washthe organic layer was washed with sat. NaHCO3 aq. solution, brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe crude material was continued to the next step with no further purification

Quellen und Nachweise

ORD-Eintrag
ord-db5eb5b91acf4718aa92668458aa9664
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09040690B2

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