Sodium Bicarbonate → HCID 18338942, compound

HRID 2298549Notes

Reaction equation

HRID 2298549 reaction equation
[CH3:1][C@@H:2]([C@@H:18]([OH:25])[C:19]#[C:20][Si](C)(C)C)[C:3]([N:5]1[C@@H:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][O:7][C:6]1=[O:17])=[O:4].[F-].[K+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:1][C@@H:2]([C@@H:18]([OH:25])[C:19]#[CH:20])[C:3]([N:5]1[C@@H:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][O:7][C:6]1=[O:17])=[O:4]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 522689Potassium FluorideHCID 69463173HCID 69463173, compound

Product 1

HCID 18338942HCID 18338942, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (4S)-N-[(2S,3R)-2-methyl-3-hydroxy-5-trimethylsilyl-4-pentynoyl]-4-benzyl-2-oxazolidinone (0.13 g) in 3 mL of dimethylformamide was treated with 48% aqueous HF (2.6 uL) and KF.2H2O at ambient temperature for 100 min. Upon completion of the reaction, saturated aqueous sodium bicarbonate was added to neutralize the HF, and the mixture was extracted three times with equal portions of ether. The organic extracts were combined, filtered, and dried over MgSO4. Filtration and evaporation gave the crude product, which was purified by silica gel chromatography (3:2 hexanes/ethyl acetate) to yield 64 mg of product.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted three times with equal portions of ether
  3. filtrationfiltered
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and evaporation
  6. customgave the crude product, which
  7. customwas purified by silica gel chromatography (3:2 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-669837c1b428447489ed6a74c48cb4e2
Source dataset
uspto-grants-2002_12
Patent number
US06492562B1

Reaction notes

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