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

HRID 1243179ノート

反応式

HRID 1243179 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7360Tetrahydrofurfuryl alcohol溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-87b5cc174ed44f29966f2600f352099c
出典データセット
uspto-grants-2006_10
特許番号
US07115740B2

反応ノート

読み込み中…