Diisopropylethylamine → HCID 59075097, compound

HRID 2184339Notes

Reaction equation

HRID 2184339 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C@@H:15]([CH:16]=O)[CH2:14][C:13]([CH3:19])([CH3:18])[C:12]1=[O:20])[CH3:2].COP([CH2:28][C:29](=[O:39])[C:30]1[O:31][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:34]=1)(=O)OC.[Cl-].[Li+].C(N(C(C)C)CC)(C)C>C(#N)C>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C@@H:15](/[CH:16]=[CH:28]/[C:29](=[O:39])[C:30]2[O:31][C:32]([C:35]([F:38])([F:36])[F:37])=[CH:33][CH:34]=2)[CH2:14][C:13]([CH3:19])([CH3:18])[C:12]1=[O:20])[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 433294Lithium ChlorideHCID 20792910HCID 20792910, compoundHCID 59075101HCID 59075101, compound

Product 1

HCID 59075097HCID 59075097, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 7-((R)-5-formyl-3,3-dimethyl-2-oxo-pyrrolidin-1-yl)-heptanoic acid ethyl ester. (360 mg, 1.21 mmol) and [2-oxo-2-(5-trifluoromethyl-furan-2-yl)-ethyl]-phosphonic acid dimethyl ester (344 mg, 1.21 mmol)(prepared from 5-trifluoromethyl-furan-2-carboxylic acid as described herein) in acetonitrile (14 mL), were added lithium chloride (62 mg, 1.21 mmol) and diisopropylethyl amine (0.214 mL, 1.21 mmol). The reaction flask was left stirring at room temperature over the weekend. The reaction was then quenched with a saturated solution of ammonium chloride and extracted with ethyl acetate. The organic phase was then washed with brine and dried over magnesium sulfate, and the crude was purified on silicagel column using hexane:ethyl acetate 2:1. Evaporation of the solvent gave 280 mg of 7-{(R)-3,3-dimethyl-2-oxo-5-[(E)-3-oxo-3-(5-trifluoromethyl-furan-2-yl)-propenyl]-pyrrolidin-1-yl}-heptanoic acid ethyl ester.

Workup

  1. waitThe reaction flask was left
  2. customThe reaction was then quenched with a saturated solution of ammonium chloride
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was then washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customthe crude was purified on silicagel column
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-951471dd195e44a9839c32b958834e88
Source dataset
uspto-grants-2005_05
Patent number
US06900336B2

Reaction notes

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