Lithium hydroxide, monohydrate → 2(R)-benzyl-3-(morpholinocarbonyl)propionic acid

HRID 1768855Notes

Reaction equation

HRID 1768855 reaction equation
[OH2:1].[OH-].[Li+].C([C@H]1COC(=O)N1[C:17](=[O:35])[C@H:18]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:19][C:20]([N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=[O:21])C1C=CC=CC=1>O1CCCC1.O>[CH2:28]([C@H:18]([CH2:19][C:20]([N:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1)=[O:21])[C:17]([OH:35])=[O:1])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 15045752(4S)-(-)-4-benzyl-N-[2(R)-benzyl-3-(morpholinocarbonyl)propionyl]-2-oxazolidinone

Product 1

HCID 142130822(R)-benzyl-3-(morpholinocarbonyl)propionic acidYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

711 mg (16.9 mmole) of lithium hydroxide monohydrate were added, whilst ice-cooling, to a solution of 3.70 g (8.5 mmole) of (4S)-(-)-4-benzyl-N-[2(R)-benzyl-3-(morpholinocarbonyl)propionyl]-2-oxazolidinone (prepared as described in Preparation 10) in a mixture of 80 ml of tetrahydrofuran and 30 ml of water, and the mixture was then stirred at the same temperature for 3 hours. At the end of this time, the tetrahydrofuran was stripped from the reaction mixture by distillation under reduced pressure, and the residue was mixed with a 10% w/v aqueous solution of sodium hydroxide and then extracted with methylene chloride. The aqueous layer was adjusted to a pH value of 1 by the addition of concentrated hydrochloric acid, whilst ice-cooling, and was again extracted with methylene chloride. The latter methylene chloride extracts were combined, dried over anhydrous magnesium sulfate and concentrated by distillation under reduced pressure to afford 1.75 g (yield 75%) of the title compound as a white oily substance.

Workup

  1. distillationAt the end of this time, the tetrahydrofuran was stripped from the reaction mixture by distillation under reduced pressure
  2. additionthe residue was mixed with a 10% w/v aqueous solution of sodium hydroxide
  3. extractionextracted with methylene chloride
  4. additionThe aqueous layer was adjusted to a pH value of 1 by the addition of concentrated hydrochloric acid, whilst ice-
  5. temperaturecooling
  6. extractionwas again extracted with methylene chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated by distillation under reduced pressure

Sources & evidence

ORD record
ord-047fbbb480394c85af0feec1e42d4a54
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

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