Lithium Hydroxide → (4s,5r)-3-benzoyl-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid

HRID 1837831Notes

Reaction equation

HRID 1837831 reaction equation
[C:1]([N:9]1[C@@H:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:12]([C:20]([O:22]CC)=[O:21])[O:11][C:10]1([CH3:26])[CH3:25])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1>[C:1]([N:9]1[C@@H:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:12]([C:20]([OH:22])=[O:21])[O:11][C:10]1([CH3:26])[CH3:25])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 12040974HCID 12040974, compound

Product 1

HCID 10131335(4s,5r)-3-benzoyl-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acidYield 96.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4S-trans)-3-Benzoyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid, ethyl ester (1.56 g) was dissolved in THF (10 ml) at room temperature and LiOH (4.63 ml, 1M in H2O) was added dropwise. Initially, a bi-phasic mixture was observed, but after the addition of the last quantity of LiOH and stirring for 5 minutes the solution became homogeneous. After further stirring for ½ hour, the reaction mixture was quenched with aqueous 1N HCl (4.63 ml), and diluted with EtOAc and saturated NaCl. The H2O layer (pH=3) was twice extracted with EtOAc, and the combined organic phase dried with MgSO4. The solvent was removed in vacuo to give 1.39 g of the title product acid (97%) which was homogeneous by TLC and 1H NMR.

Workup

  1. stirringAfter further stirring for ½ hour
  2. customthe reaction mixture was quenched with aqueous 1N HCl (4.63 ml)
  3. additiondiluted with EtOAc and saturated NaCl
  4. extractionThe H2O layer (pH=3) was twice extracted with EtOAc
  5. dry with materialthe combined organic phase dried with MgSO4
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e9e5f735fe4e489fa8eb3a24d906d0b5
Source dataset
uspto-grants-2004_08
Patent number
US06784304B2

Reaction notes

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