Lithium Hydroxide → 2(R)-benzyl-3-(N-benzyl-N-methylaminocarbonyl)propionic acid

HRID 1768859Notes

Reaction equation

HRID 1768859 reaction equation
[OH-:1].[Li+].[CH2:3]([C@H:10]([CH2:22][C:23]([N:25]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH3:26])=[O:24])[C:11](N1[C@H](C(C)C)COC1=O)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCCC1.O>[CH2:3]([C@H:10]([CH2:22][C:23]([N:25]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH3:26])=[O:24])[C:11]([OH:12])=[O:1])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 186581703-[2(R)-benzyl-4-(N-benzyl-N-methylamino)-4-oxobutyryl]-4(R)-isopropyl-2-oxazolidinone

Product 1

HCID 150457542(R)-benzyl-3-(N-benzyl-N-methylaminocarbonyl)propionic acidYield 28.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

80 mg (1.89 mmole) of lithium hydroxide were added to a solution of 400 mg (0.95 mmole) of 3-[2(R)-benzyl-4-(N-benzyl-N-methylamino)-4-oxobutyryl]-4(R)-isopropyl-2-oxazolidinone (prepared as described in Preparation 14) in a mixture of 10 ml of tetrahydrofuran and 4 ml of water, and the mixture was stirred at room temperature for 5 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was mixed with methylene chloride. The mixture was then extracted with a 10% w/v aqueous solution of sodium hydroxide. The aqueous layer was adjusted to a pH value of 2.0 by the addition of citric acid and was then extracted with methylene chloride. The methylene chloride extracts were combined, dried over anhydrous magnesium sulfate and concentrated by distillation under reduced pressure, to afford a colorless oil. This oil was triturated with hexane and the powder which deposited was collected by filtration and then recrystallized from diisopropyl ether, to afford 84 mg of the title compound as needles, melting at 119°-121° C.

Workup

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. additionthe resulting residue was mixed with methylene chloride
  3. extractionThe mixture was then extracted with a 10% w/v aqueous solution of sodium hydroxide
  4. additionThe aqueous layer was adjusted to a pH value of 2.0 by the addition of citric acid
  5. extractionwas then extracted with methylene chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated by distillation under reduced pressure
  8. customto afford a colorless oil
  9. customThis oil was triturated with hexane
  10. filtrationthe powder which deposited was collected by filtration
  11. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-3402cde4480b4b0d8198617440dbb6e3
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

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