Hydrochloric Acid → (+/-)-{3-{[2-(4,5-Diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzoylamino}acetic acid

HRID 2305229Notes

Reaction equation

HRID 2305229 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH:19]([CH2:24][C:25]4[CH:26]=[C:27]([CH:37]=[CH:38][CH:39]=4)[C:28]([NH:30][CH2:31][C:32]([O:34]CC)=[O:33])=[O:29])[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Li+].O.Cl>O1CCCC1.CO.O>[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH:19]([CH2:24][C:25]4[CH:26]=[C:27]([CH:37]=[CH:38][CH:39]=4)[C:28]([NH:30][CH2:31][C:32]([OH:34])=[O:33])=[O:29])[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 9892894HCID 9892894, compound

Product 1

HCID 9913581(+/-)-{3-{[2-(4,5-Diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzoylamino}acetic acidYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of ethyl (±)-{3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzoylamino}acetate (136.8 mg, 0.263 mmol) in tetrahydrofuran (4 ml) was added a solution of lithium hydroxide-water (22.1 mg, 0.526 mmol) in MeOH-water (1:1) (2.8 ml) at 5° C. and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added 1N-hydrochloric acid (0.8 ml) at 5° C. and extracted with EtOAc. The organic layer was washed with water and brine successively, dried over magnesium sulfate, and evaporated in vacuo to give (±)-{3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzoylamino}acetic acid (129.0 mg, 100%).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water and brine successively
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-25bd1906430e49c681eb0b5ddbe753bf
Source dataset
uspto-grants-2002_08
Patent number
US06437146B1

Reaction notes

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