Lithium hydroxide, monohydrate → 3-{4-[2-(4-tert-Butoxycarbonylaminophenyl)ethoxy]phenyl}-2-ethoxypropanoic acid

HRID 987271Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 987271
O.[OH-].[Li+].C([O:6][C:7](=[O:36])[CH:8]([O:33][CH2:34][CH3:35])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:21][CH:20]=2)=[CH:12][CH:11]=1)C>O.O1CCCC1>[C:29]([O:28][C:26]([NH:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][CH2:17][O:16][C:13]2[CH:12]=[CH:11][C:10]([CH2:9][CH:8]([O:33][CH2:34][CH3:35])[C:7]([OH:36])=[O:6])=[CH:15][CH:14]=2)=[CH:24][CH:23]=1)=[O:27])([CH3:32])([CH3:31])[CH3:30]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 22988408Ethyl 3-(4-[2-(4-tert-butoxycarbonylaminophenyl)ethoxy]phenyl}-2-ethoxypropanoate

Produkt 1

HCID 229884463-{4-[2-(4-tert-Butoxycarbonylaminophenyl)ethoxy]phenyl}-2-ethoxypropanoic acidAusbeute 98,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium hydroxide hydrate (77 mg; 1.85 mmole) in water (5.5 ml) was slowly added to a solution of 3-{4-[2-(4-tert-butoxycarbonylaminophenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl ester (described in Example 38) (0.77 g; 1.68 mmole) in tetrahydrofuran (7.6 ml). After stirring at room temperature for 4 hours the reaction mixture was kept in a freezer for 4 days. Tetrahydrofuran was removed by evaporation in vacuo. More water was added and the mixture was acidified with hydrochloric acid to pH1. The product was extracted with ethyl acetate, washed twice with water, dried (sodium sulfate), filtered and the solvent was evaporated in vacuo to give 0.712 g (98.7% yield) of 3-{4-[2-(4-tert-butoxycarbonylaminophenyl)ethoxy]phenyl}-2-ethoxypropanoic acid.

Aufarbeitung

  1. waitwas kept in a freezer for 4 days
  2. customTetrahydrofuran was removed by evaporation in vacuo
  3. additionMore water was added
  4. extractionThe product was extracted with ethyl acetate
  5. washwashed twice with water
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. customthe solvent was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f06c1de465774ebdb6b6e6c34cf1d81a
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06630600B1

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