Imidazole → (S)-3-{2-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methyl-but-3-enoyl}-4-isopropyl-oxazolidin-2-one

HRID 2285372Notes

Reaction equation

HRID 2285372 reaction equation
[OH:1][CH:2]([C:4]([CH3:18])([CH:16]=[CH2:17])[C:5]([N:7]1[C@@H:11]([CH:12]([CH3:14])[CH3:13])[CH2:10][O:9][C:8]1=[O:15])=[O:6])[CH3:3].[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].N1C=CN=C1>CN(C)C=O>[C:22]([Si:19]([CH3:21])([CH3:20])[O:1][CH:2]([C:4]([CH3:18])([CH:16]=[CH2:17])[C:5]([N:7]1[C@@H:11]([CH:12]([CH3:13])[CH3:14])[CH2:10][O:9][C:8]1=[O:15])=[O:6])[CH3:3])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 795Imidazole2×HCID 28928tert-Butyldimethylsilyl chloride2×HCID 86709666(S)-3-[2-(1-Hydroxy-ethyl)-2-methyl-but-3-enoyl]-4-isopropyl-oxazolidin-2-one

Product 1

HCID 86709667(S)-3-{2-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methyl-but-3-enoyl}-4-isopropyl-oxazolidin-2-oneYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (S)-3-[2-(1-hydroxy-ethyl)-2-methyl-but-3-enoyl]-4-isopropyl-oxazolidin-2-one (1.742 g, 6.809 mmol) and tert-butyldimethylsilyl chloride (1.231 g, 8.17 mmol) in anhydrous N,N-dimethylformamide (10 mL) was treated with imidazole (927 mg, 13.618 mmol). After stirring at room temperature for 6 h, tert-butyldimethylsilyl chloride (1.1 g, 7.3 mmol) and imidazole (950 mg, 13.954 mmol) were added. After stirring at room temperature for 12 days, the reaction was quenched with a saturated solution of ammonium chloride. The aqueous layer was extracted with diethyl ether (2×). The organics were combined, dried over anhydrous sodium sulfate, filtered and the volatiles were removed in vacuo. The residue was purified by silica gel chromatography using a 100 g Isolute cartridge eluted with a continuous gradient of iso-hexanes/diethyl ether 1:0 to 1:1 to afford the title compound (1.729 g, 69%) as an undetermined mixture of diastereoisomers and as a yellow oil. LCMS (m/z) 370.1 [M+H], Tr=3.96 min and 370.1 [M+H], Tr=4.22 min.

Workup

  1. stirringAfter stirring at room temperature for 12 days
  2. customthe reaction was quenched with a saturated solution of ammonium chloride
  3. extractionThe aqueous layer was extracted with diethyl ether (2×)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe volatiles were removed in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluted with a continuous gradient of iso-hexanes/diethyl ether 1:0 to 1:1

Sources & evidence

ORD record
ord-08366674433248d8982006cbd0d56428
Source dataset
uspto-grants-2015_09
Patent number
US09145441B2

Reaction notes

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