Lithium Hydroxide → HCID 15045771, compound

HRID 1768864Notes

Reaction equation

HRID 1768864 reaction equation
[OH-:1].[Li+].[CH2:3]([C@H:10]([CH2:22][C:23]([N:25]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]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]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]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 18658171HCID 18658171, compound

Product 1

HCID 15045771HCID 15045771, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

100 mg (2.42 mmole) of lithium hydroxide were added to a solution of 500 mg (1.21 mmole) of 3-[2(R)-benzyl-4-(N-cyclohexyl-N-methylamino)-4-oxobutyryl]-4(S)-isopropyl-2-oxazolidinone (which had been prepared by a similar procedure to those described in Preparations 12-14) 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 an aqueous solution of sodium bicarbonate and extracted with methylene chloride. The aqueous layer was adjusted to a pH value of 2 by the addition of an aqueous solution of citric acid and was then extracted with methylene chloride. The latter methylene chloride extract was dried over anhydrous magnesium sulfate and concentrated by distillation under reduced pressure, to afford 130 mg of the title compound as an amorphous product.

Workup

  1. customhad been prepared by a similar procedure to
  2. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  3. additionthe resulting residue was mixed with an aqueous solution of sodium bicarbonate
  4. extractionextracted with methylene chloride
  5. additionThe aqueous layer was adjusted to a pH value of 2 by the addition of an aqueous solution of citric acid
  6. extractionwas then extracted with methylene chloride
  7. extractionThe latter methylene chloride extract
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. concentrationconcentrated by distillation under reduced pressure

Sources & evidence

ORD record
ord-56e490d3c4a64b4c8b8ce7b18ddccb1c
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

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