Imidazole → HCID 89852239, compound

HRID 627071Notes

Reaction equation

HRID 627071 reaction equation
[OH:1][CH2:2][C@@H:3]([N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16])[CH:4]=[CH2:5].N1C=CN=C1.[C:22]([Si:26]([CH3:29])([CH3:28])Cl)([CH3:25])([CH3:24])[CH3:23].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Si:26]([O:1][CH2:2][C@@H:3]([N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16])[CH:4]=[CH2:5])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 109984602-[(2S)-1-hydroxybut-3-en-2-yl]isoindole-1,3-dione2×

Product 1

HCID 89852239HCID 89852239, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-2-(1-hydroxybut-3-en-2-yl)isoindoline-1,3-dione (Intermediate 1, 69.4 g, 319.49 mmol) and imidazole (26.1 g, 383.39 mmol) in methylene chloride (160 mL), at ambient temperature under an atmosphere of nitrogen, was added tert-butyldimethylchlorosilane (55.4 g, 367.41 mmol) as a solid. This addition was performed over approximately ten minutes. Warming of the mixture was observed during this addition. After two hours stirring, the solution was poured into a saturated solution of aqueous sodium bicarbonate (approximately 150 mL); this biphasic mixture was shaken, and the organic layer was separated. The aqueous layer was back-extracted three times with 200 mL methylene chloride each time. The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated in vacuo. The desired product was obtained as a pale yellow solid after drying overnight under high vacuum (107 g, 101%).

Workup

  1. additionThis addition
  2. waitwas performed over approximately ten minutes
  3. temperatureWarming of the mixture
  4. additionwas observed during this addition
  5. stirringthis biphasic mixture was shaken
  6. customthe organic layer was separated
  7. extractionThe aqueous layer was back-extracted three times with 200 mL methylene chloride each time
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-541c15543b9b47ae81d0f84dea720712
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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