Sodium Hydroxide → (S)-(+)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylpropionic acid

HRID 1243179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1243179
[C:1]([Si:5]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[O:6][CH2:7][C@H:8]([CH3:13])[C:9]([O:11]C)=[O:10])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCCC1CO>[C:1]([Si:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[O:6][CH2:7][C@H:8]([CH3:13])[C:9]([OH:11])=[O:10])([CH3:2])([CH3:3])[CH3:4]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 11302759(2S)-3-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-2-methylpropanoic Acid Methyl Ester

Produkt 1

HCID 10665033(S)-(+)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylpropionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7360Tetrahydrofurfuryl alcoholLösungsmittel

Versuchsvorschrift

This ester (3.15 g, 8.85 mmol) was dissolved in 3:1 tetrahydrofuran-methanol (30 mL) and saponified with aqueous sodium hydroxide (1.0 N, 10.0 mL, 10.0 mmol) overnight at ambient temperature. After concentration, the residue was partitioned between ethyl acetate and water and then acidified (to pH 4–5) with 0.5N aqueous hydrochloric acid. The organic phase was washed with water and brine, dried over anhydrous sodium sulfate and concentrated. Purification was carried out with multiple flash chromatography runs using the Biotage system. Pure fractions from each run were combined and concentrated to yield (S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylpropionic acid as an oil that solidified to a tacky white solid in the cold. (Yield 2.10 g, 69.2%).

Aufarbeitung

  1. concentrationAfter concentration
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customPurification
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-87b5cc174ed44f29966f2600f352099c
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115740B2

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