Sodium Hydroxide → sodium 3-[(2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidin-1-ylmethyl]phenoxyacetate

HRID 431762Notes

Reaction equation

HRID 431762 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C@H:18]3[CH2:22][C@@H:21]([OH:23])[CH2:20][N:19]3[CH2:24][C:25]3[CH:26]=[C:27]([CH:35]=[CH:36][CH:37]=3)[O:28][CH2:29][C:30]([O:32]CC)=[O:31])[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+:39]>CO.O1CCOCC1>[C:1]1([C:7]2[N:8]=[C:9]([C@H:18]3[CH2:22][C@@H:21]([OH:23])[CH2:20][N:19]3[CH2:24][C:25]3[CH:26]=[C:27]([CH:35]=[CH:36][CH:37]=3)[O:28][CH2:29][C:30]([O-:32])=[O:31])[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.[Na+:39]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11156247ethyl 3-{[(2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidin-1-yl]methyl}phenoxyacetate

Product 1

HCID 86759294sodium 3-[(2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidin-1-ylmethyl]phenoxyacetate

Reagents, catalysts & solvents 1

HCID 21966525Dioxane MethanolSolvent

Procedure

To a solution of ethyl 3-{[(2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidin-1-yl]methyl}phenoxyacetate (353 mg) in MeOH:1,4-dioxane (1:1, 10 mL) was added 1N NaOH solution (0.744 mL) at 5° C., and the mixture was stirred at room temperature for 4 hours. The reaction mixture was evaporated and Et2O was added thereto. The resulting solid was collected by filtration to give sodium 3-[(2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidin-1-ylmethyl]phenoxyacetate (327.7 mg).

Workup

  1. customThe reaction mixture was evaporated
  2. additionEt2O was added
  3. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-6b61b5d222df49f9976248335765a857
Source dataset
uspto-grants-2003_12
Patent number
US06660759B1

Reaction notes

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