3-(4-Formylbenzoylamino)propionic acid methyl ester → HCID 59518064, compound

HRID 1914298Notes

Reaction equation

HRID 1914298 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[O:15])=[CH:10][CH:9]=1.[CH3:18][C:19]([CH3:25])([CH2:23][CH3:24])[CH2:20][Mg]Br>O1CCCC1>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([OH:15])[CH2:24][CH2:23][C:19]([CH3:25])([CH3:20])[CH3:18])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 161003253-(4-Formylbenzoylamino)propionic acid methyl esterHCID 178444607HCID 178444607, compound

Product 1

HCID 59518064HCID 59518064, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-(4-Formyl-benzoylamino)-propionic acid methyl ester (4.8 g, 20.43 mmol) is dissolved in the anhydrous tetrahydrofuran (THF) (75 mL) and cooled to 0° C. under nitrogen. 2,2-Dimethyl-butyl magnesium bromide (16.3 mL, 1.5M solution in THF, 24.5 mmol) is then added slowly to the solution by addition funnel. The reaction is allowed to stir at 0° C. for 1 hour and the ice bath is removed. The reaction is monitored by TLC or HPLC to determine complete consumption of the aldehyde. The reaction is cooled back down to 0° C. and 1.0N hydrogen chloride solution is dropped in to quench. The solids are dissolved with enough water and the solution is diluted with ether. The two phases are separated and the organic layer is washed with brine, dried over anhydrous sodium sulfate and concentrated. The alcohol (1.6 g, 4.98 mmol) is purified by column chromatography.

Workup

  1. customthe ice bath is removed
  2. customconsumption of the aldehyde
  3. temperatureThe reaction is cooled back down to 0° C. and 1.0N hydrogen chloride solution
  4. additionis dropped in
  5. customto quench
  6. dissolutionThe solids are dissolved with enough water
  7. additionthe solution is diluted with ether
  8. customThe two phases are separated
  9. washthe organic layer is washed with brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-42fee93644654dacbf8aa5a0ec9e4a76
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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