Water → HCID 66653180, compound

HRID 1524282Notes

Reaction equation

HRID 1524282 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:28])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C@@H:14]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=3)[C:15]2=[O:27])[CH:8]=1>O1CCCC1>[C:25]([C:22]1[CH:21]=[CH:20][C:19]([N:16]2[CH2:17][CH2:18][C@@H:14]([O:13][C:9]3[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=3)[C:6]([OH:28])=[O:5])[C:15]2=[O:27])=[CH:24][CH:23]=1)#[N:26]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 66653230HCID 66653230, compound

Product 1

HCID 66653180HCID 66653180, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add water (2 mL) followed by lithium hydroxide (0.62 g, 14.9 mmol) to a solution of 3-[(R)-1-(4-cyano-phenyl)-2-oxo-pyrrolidin-3-yloxy]-benzoic acid methyl ester (1.00 g, 2.98 mmol) of in tetrahydrofuran (4 mL). Stir the mixture overnight at room temperature then concentrate under reduced pressure to remove volatile organics. Wash the concentrated aqueous mixture with EtOAc and then acidify to pH 4 using a 0.5 M solution of citric acid. Extract the mixture with EtOAc and concentrate under reduced pressure to provide 0.74 g of 3-[(R)-1-(4-cyano-phenyl)-2-oxo-pyrrolidin-3-yloxy]-benzoic acid as a solid.

Workup

  1. concentrationthen concentrate under reduced pressure
  2. customto remove volatile organics
  3. washWash the concentrated aqueous mixture with EtOAc
  4. extractionExtract the mixture with EtOAc
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-51b979a0b033443a9b9a6481c8f13162
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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