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

HRID 1178568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178568
[OH: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>[OH: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 73017203Methyl 2-{[2-(4-hydroxyphenyl)ethyl]thio}-3-[4-(2-{4-[(methylsulfonyl)oxy]phenoxy}ethyl)phenyl]propanoate

Produkt 1

HCID 102179842-{[2-(4-Hydroxyphenyl)ethyl]thio}-3-[4-(2-{4-[(methylsulfonyl)oxy]-phenoxy}ethyl)phenyl]propanoic acidAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 2-{[2-(4-hydroxyphenyl)ethyl]thio}-3-[4-(2-{4-[(methylsulfonyl)oxy]phenoxy}-ethyl)phenyl]propanoate (105 mg, 0.2 mmol) was dissolved in 6.5 ml of a 7:1 mixture of THF and water and cooled on an ice-bath. Lithium hydroxide (9.4 mg, 0.4 mmol) was added. Water was added to the reaction mixture after 24 hours of stirring at room temperature. The THF was evaporated under reduced pressure and the residue was acidified with 1M hydrochloric acid. The water phase was extracted with EtOAc (×3), 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) to give 74 mg of the desired product (yield 97%) as an oil.

Aufarbeitung

  1. temperaturecooled on an ice-bath
  2. customThe THF was evaporated under reduced pressure
  3. extractionThe water phase was extracted with EtOAc (×3)
  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-3e5dadf2e54347caa57618ba3d6a621c
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276539B2

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