Triethylamine → (R)-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-propionic acid methyl ester

HRID 31553

반응식

HRID 31553 반응식
[OH:1][C@H:2]([CH2:7][OH:8])[C:3]([O:5][CH3:6])=[O:4].C(N(CC)CC)C.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].[Cl-].[NH4+]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Si:16]([O:8][CH2:7][C@@H:2]([OH:1])[C:3]([O:5][CH3:6])=[O:4])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 9920382(R)-Methyl 2,3-dihydroxypropanoate

생성물 1

HCID 45037054(R)-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-propionic acid methyl ester수율 59.1%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

The compound of Example 68-1 (308 mg, 2.57 mmol) was dissolved in methylene chloride (10 ml), and thereto were added triethylamine (704 mg, 6.95 mmol), 4-dimethylaminopyridine (33 mg, 0.27 mmol), and t-butyldimethylsilyl chloride (524 mg, 3.48 mmol). The mixture was stirred at room temperature for 2 hours, and thereto was added a saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give the title compound (356 mg, 57%).

후처리

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with water and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-8b75715629c248668cea444024befa68
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425642B2

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