Lithium Hydroxide → HCID 46186809, compound

HRID 2060229Notes

Reaction equation

HRID 2060229 reaction equation
[OH-].[Li+].C([O:5][C:6]([C:8]1([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=3)=[CH:26][CH:25]=2)[CH2:12][CH2:11][N:10]([C:13](=[O:21])[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])C>C(O)C.O>[C:36]([C:33]1[CH:34]=[CH:35][C:30]([C:27]2[CH:26]=[CH:25][C:24]([O:23][CH2:22][C:8]3([C:6]([OH:7])=[O:5])[CH2:12][CH2:11][N:10]([C:13](=[O:21])[C:14]4[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=4)[CH2:9]3)=[CH:29][CH:28]=2)=[CH:31][CH:32]=1)#[N:37]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59322207HCID 59322207, compound

Product 1

HCID 46186809HCID 46186809, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Lithium hydroxide (16 mg, 0.67 mmol) was added to a stirred solution of 3-(4′-cyano-biphenyl-4-yloxymethyl)-1-(4-fluoro-benzoyl)-pyrrolidine-3-carboxylic acid ethyl ester (see Preparation 29) (105 mg, 0.22 mmol) in ethanol (1 mL) and water (1 mL). The resulting mixture was stirred at RT for 5 hours. The mixture was concentrated under reduced pressure to remove ethanol and the residue was partitioned between ethyl acetate (5 mL) and 2M HCl aqueous solution (5 mL). The organic layer was washed with brine (5 mL), dried over magnesium sulphate and concentrated under reduced pressure to afford a white solid. This was recrystallised from isopropyl alcohol (2.5 mL) to afford the title compound as a white solid (76 mg, 77%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto remove ethanol
  3. customthe residue was partitioned between ethyl acetate (5 mL) and 2M HCl aqueous solution (5 mL)
  4. washThe organic layer was washed with brine (5 mL)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customto afford a white solid
  8. customThis was recrystallised from isopropyl alcohol (2.5 mL)

Sources & evidence

ORD record
ord-3d0f20a082e841458930622bab4ef443
Source dataset
uspto-grants-2012_10
Patent number
US08278343B2

Reaction notes

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