Lithium Hydroxide → 2-{[2-(4-Fluorophenyl)ethyl]thio}-3-[4-(2-{4-[(methylsulfonyl)oxy]-phenoxy}ethyl)phenyl]propanoic acid

HRID 1178569Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178569
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][S:10][CH:11]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][S:33]([CH3:36])(=[O:35])=[O:34])=[CH:28][CH:27]=3)=[CH:19][CH:18]=2)[C:12]([O:14]C)=[O:13])=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][S:10][CH:11]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][O:25][C:26]3[CH:27]=[CH:28][C:29]([O:32][S:33]([CH3:36])(=[O:35])=[O:34])=[CH:30][CH:31]=3)=[CH:19][CH:18]=2)[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 86600806HCID 86600806, Verbindung

Produkt 1

HCID 103115412-{[2-(4-Fluorophenyl)ethyl]thio}-3-[4-(2-{4-[(methylsulfonyl)oxy]-phenoxy}ethyl)phenyl]propanoic acidAusbeute 33,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 2-{[2-(4-fluorophenyl)ethyl]thio}-3-[4-(2-{4-[(methylsulfonyl)oxy]-phenoxy}ethyl)phenyl]propanoate (77 mg, 0.14 mmol) was dissolved in 2.5 ml of a 4:1 mixture of THF and water and cooled on an ice-bath. Lithium hydroxide (6.9 mg, 0.29 mmol) was added. Water was added after 2 days of stirring at room temperature. The THF was evaporated under reduced pressure. The aqueous phase was acidified with 1M HCl and extracted with EtOAc three times. The organic phases were pooled, washed (water, brine), dried (MgSO4) and evaporated. The crude product was purified using preparative HPLC (eluent: CH3CN/5% CH3CN-waterphase containing 0.1M NH4Oac). 24 mg of the desired product (yield 30%) was obtained as an oil.

Aufarbeitung

  1. temperaturecooled on an ice-bath
  2. customThe THF was evaporated under reduced pressure
  3. extractionextracted with EtOAc three times
  4. washwashed (water, brine)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was purified
  8. additionHPLC (eluent: CH3CN/5% CH3CN-waterphase containing 0.1M NH4Oac)

Quellen und Nachweise

ORD-Eintrag
ord-8d6bc0a54b66457da1fd6c1597e5dcba
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276539B2

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