Lithium Hydroxide → 2-(4(S)-Phenyloxazolidin-2-on-3-yl)propanoic acid

HRID 2207140Notes

Reaction equation

HRID 2207140 reaction equation
[C:1]1([C@H:7]2[CH2:11][O:10][C:9](=[O:12])[N:8]2[CH:13]([CH3:18])[C:14]([O:16]C)=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH-].N1CCC1=O>CO.O>[C:1]1([C@H:7]2[CH2:11][O:10][C:9](=[O:12])[N:8]2[CH:13]([CH3:18])[C:14]([OH:16])=[O:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 1367212-AzetidinoneHCID 66587141Methyl 2-(4(S)-phenyloxazolidin-2-on-3-yl)propanoate

Product 1

HCID 665870702-(4(S)-Phenyloxazolidin-2-on-3-yl)propanoic acidYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-(4(S)-phenyloxazolidin-2-on-3-yl)propanoate (1 g, 4.01 mmol) in 35 mL of MeOH was added, at 0° C., 14.3 mL (12.04 mmol) of a 0.84 M solution of LiOH in water. The reaction mixture was then stirred for 3 h. at ambient temperature. Upon complete hydrolysis of the azetidinone, the MeOH was removed by evaporation, the crude residue dissolved in CH2Cl2 and treated with saturated aqueous NaCl. The resulting organic layer was dried (MgSO4) and evaporated to afford the title compound (racemic mixture) as a white solid (0.906 g, 96%); 1H NMR (CDCl3) δ 1.13/1.57 (d/d, J=7.5 Hz, 3H), 3.75/4.50 (q/q, J=7.5 Hz, 1H), 4.10-4.16 (m, 1H), 4.62-4.72 (m, 1H), 4.92-5.03 (m, 1H), 7.32-7.43 (m, 5H).

Workup

  1. customthe MeOH was removed by evaporation
  2. dissolutionthe crude residue dissolved in CH2Cl2
  3. additiontreated with saturated aqueous NaCl
  4. dry with materialThe resulting organic layer was dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-f54a3032e8504e9da62a3c65d6e4fadf
Source dataset
uspto-grants-2016_06
Patent number
US09376424B2

Reaction notes

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