2-Propenoic acid, 3-phenyl-, methyl ester → HCID 15941322, compound

HRID 2059808Notes

Reaction equation

HRID 2059808 reaction equation
[CH:1]([N:4]([CH:14]([CH3:16])[CH3:15])[C:5](=[O:13])[CH2:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)([CH3:3])[CH3:2].[Li+].CC([N-]C(C)C)C.[C:25]([O:35][CH3:36])(=[O:34])[CH:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1>[CH:14]([N:4]([CH:1]([CH3:2])[CH3:3])[C:5](=[O:13])[CH:6]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[CH:27]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:26][C:25]([O:35][CH3:36])=[O:34])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 76442-Propenoic acid, 3-phenyl-, methyl esterHCID 2724682Lithium diisopropylamideHCID 57429229N,N-Di(propan-2-yl)-2-(pyridin-3-yl)acetamide

Product 1

HCID 15941322HCID 15941322, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of N,N-diisopropyl-2-pyridin-3-ylacetamide (740 mg, 3.36 mmol) in dry THF (30 mL) was added a solution of LDA (1.5 M) in THF (4.5 mL, 6.72 mmol). The reaction mixture was stirred at 0° C. for 30 min and then cooled to −78° C. Solid methyl cinnamate (654 mg, 4.031 mmol) was added in one portion. The cooling bath was removed and the reaction mixture was allowed to warm up to room temperature. After 1.5 h, the reaction was quenched by adding a saturated aqueous solution of NH4Cl and partitioned between CH2Cl2 and saturated aqueous NaHCO3. The aqueous layer was extracted with CH2Cl2 (3×). The combined organic layers were dried over anhydrous Na2SO4 and concentrated. The resulting red viscous liquid was purified by flash chromatography using a linear gradient of 0% to 5% MeOH—NH3 (90:10 v/v) in CH2Cl2. Yellow solid, single diastereomer.

Workup

  1. temperaturecooled to −78° C
  2. customThe cooling bath was removed
  3. temperatureto warm up to room temperature
  4. waitAfter 1.5 h
  5. customthe reaction was quenched
  6. additionby adding a saturated aqueous solution of NH4Cl
  7. custompartitioned between CH2Cl2 and saturated aqueous NaHCO3
  8. extractionThe aqueous layer was extracted with CH2Cl2 (3×)
  9. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  10. concentrationconcentrated
  11. customThe resulting red viscous liquid was purified by flash chromatography

Sources & evidence

ORD record
ord-b2ac23d0660e43dd968d208c572aa537
Source dataset
uspto-grants-2012_10
Patent number
US08278317B2

Reaction notes

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