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

HRID 31553

Reaction equation

HRID 31553 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-8b75715629c248668cea444024befa68
Source dataset
uspto-grants-2008_09
Patent number
US07425642B2

Linked notes

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