Tetrahydrofuran → (2R)-3-(Morpholinocarbonyl)-2-(1-naphthylmethyl)-propionic acid

HRID 1768584Notes

Reaction equation

HRID 1768584 reaction equation
[OH2:1].[OH-:2].[Li+].O1[CH2:9][CH2:8][N:7]([C:10]([CH2:12][CH:13]([CH2:29][C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=[CH:32][CH:31]=2)[C:14](N2[C@@H](CC3C=CC=CC=3)COC2=O)=[O:15])=O)[CH2:6][CH2:5]1.[O:40]1CCCC1>O>[O:1]1[CH2:9][CH2:8][N:7]([C:10]([CH2:12][C@@H:13]([CH2:29][C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=[CH:32][CH:31]=2)[C:14]([OH:15])=[O:40])=[O:2])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 18658184N-[2-(morpholinocarbonyl)methyl-3-(1-naphthyl)propionyl]-(S)-(-)-4-benzyl-2-oxazolidinone

Product 1

HCID 13913945(2R)-3-(Morpholinocarbonyl)-2-(1-naphthylmethyl)-propionic acidYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

221 mg (5.27 mmole) of lithium hydroxide monohydrate were added, whilst ice-cooling, to a solution of 1.28 g (2.63 mmole) of N-[2-(morpholinocarbonyl)methyl-3-(1-naphthyl)propionyl]-(S)-(-)-4-benzyl-2-oxazolidinone (prepared as described in Preparation 3) dissolved in a mixture of 40 ml of tetrahydrofuran and 10 ml of water. The mixture was stirred at the same temperature for 3 hours, after which it was freed from the solvent by evaporation under-reduced pressure. A 10% w/v aqueous solution of sodium hydroxide was added to the residue, and the mixture was extracted with methylene chloride. The aqueous layer was separated, adjusted with hydrochloric acid to a pH value of 2 and then extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure, to afford 750 mg (87%) of the title compound as white crystals, melting at 62°-66° C.

Workup

  1. customafter which it was freed from the solvent by evaporation under-reduced pressure
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with methylene chloride
  4. customThe aqueous layer was separated
  5. extractionextracted with methylene chloride
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-4689962cde894a49b571871fea557171
Source dataset
uspto-grants-1995_01
Patent number
US05378690

Reaction notes

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