Hydrochloric Acid → HCID 86759296, compound

HRID 431764Notes

Reaction equation

HRID 431764 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C@H:18]3[CH2:22][C@H:21]([O:23][CH3:24])[CH2:20][N:19]3[CH2:25][C:26]3[CH:27]=[C:28]([CH:36]=[CH:37][CH:38]=3)[O:29][CH2:30][C:31]([O:33]CC)=[O:32])[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-].[Na+].Cl>CCO>[C:1]1([C:7]2[N:8]=[C:9]([C@H:18]3[CH2:22][C@H:21]([O:23][CH3:24])[CH2:20][N:19]3[CH2:25][C:26]3[CH:27]=[C:28]([CH:36]=[CH:37][CH:38]=3)[O:29][CH2:30][C:31]([OH:33])=[O:32])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86759297HCID 86759297, compound

Product 1

HCID 86759296HCID 86759296, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Ethyl 3-{[(2R, 4S)-2-(4,5-diphenyloxazol-2-yl)-4-methoxypyrrolidin-1-yl]methyl}phenoxyacetate (3.00 g) in EtOH (30 mL) was added 1N NaOH solution (6.00 mL) at 5° C., and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added 1N HCl (6.00 mL) at 5° C. and evaporated. The residue was extracted with EtOAc, washed with water and brine, dried (Na2SO4), and evaporated in vacuo to give 3-{[(2R, 4S)-2-(4,5-diphenyloxazol-2-yl)-4-methoxypyrrolidin-1-yl]methyl}phenoxyacetic acid (2.75 g).

Workup

  1. customevaporated
  2. extractionThe residue was extracted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-abbdc8e6ab5a4ebeb369f81e9bb6dfcc
Source dataset
uspto-grants-2003_12
Patent number
US06660759B1

Reaction notes

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