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

HRID 1243179노트

반응식

HRID 1243179 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 7360Tetrahydrofurfuryl alcohol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-87b5cc174ed44f29966f2600f352099c
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115740B2

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