Sodium hydride → HCID 12132856, compound

HRID 22971

Reaction equation

HRID 22971 reaction equation
[H-].[Na+].[O:3]=[C:4]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:5]P(=O)(OC)OC.[CH2:17]([O:19][C:20](=[O:35])[CH2:21][O:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][N:27]1[C:31](=[O:32])[CH2:30][CH2:29][C@@H:28]1[CH:33]=O)[CH3:18]>COCCOC>[CH2:17]([O:19][C:20](=[O:35])[CH2:21][O:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][N:27]1[C@@H:28](/[CH:33]=[CH:5]/[C:4](=[O:3])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:29][CH2:30][C:31]1=[O:32])[CH3:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 580181Dimethyl (2-oxoheptyl)phosphonateHCID 12132855[(Z)-4-((R)-2-formyl-5-oxo-pyrrolidin-1-yl)-but-2-enyloxy]-acetic acid ethyl ester

Product 1

HCID 12132856HCID 12132856, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of sodium hydride (95%, 0.02 g, 0.78 mmol) in 10 mL of anhydrous 1,2-dimethoxyethane at 0° C. under a nitrogen atmosphere was added dimethyl 2-oxoheptylphosphonate (0.17 mL, 0.78 mmol), and the reaction was stirred for 1 hour. A solution of [(Z)-4-((R)-2-formyl-5-oxo-pyrrolidin-1-yl)-but-2-enyloxy]-acetic acid ethyl ester (0.21 g, 0.78 mmol) in 2 mL anhydrous 1,2-dimethoxyethane was added. The reaction was allowed to come to room temperature, stirred for 3 hours and then quenched with an aqueous solution of saturated ammonium chloride. After extraction with ethyl acetate, the organic solution was dried (brine, Na2SO4), evaporated and purified by chromatography to yield {(Z)-4-[(R)-2-oxo-5-((E)-3-oxo-oct-1-enyl)-pyrrolidin-1-yl]-but-2-enyloxy}-acetic acid ethyl ester as an oil. This material was taken directly on to the next step.

Workup

  1. customto come to room temperature
  2. stirringstirred for 3 hours
  3. customquenched with an aqueous solution of saturated ammonium chloride
  4. extractionAfter extraction with ethyl acetate
  5. dry with materialthe organic solution was dried (brine, Na2SO4)
  6. customevaporated
  7. custompurified by chromatography

Sources & evidence

ORD record
ord-d46a0295b2bc4e8c8922c2c4c63235b6
Source dataset
uspto-grants-2005_02
Patent number
US06849657B2

Linked notes

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