Tetrahydrofuran → HCID 66894718, compound

HRID 19311Notes

Reaction equation

HRID 19311 reaction equation
C[O:2][C:3](=[O:24])[C@@H:4]([N:10]1[CH2:14][C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[CH:12][C:11]1=[O:23])[CH2:5][C:6]([F:9])([F:8])[CH3:7].O1CCCC1.O.[OH-].[Li+]>O>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[O:15][C:13]1[CH2:14][N:10]([C@@H:4]([CH2:5][C:6]([F:9])([F:8])[CH3:7])[C:3]([OH:24])=[O:2])[C:11](=[O:23])[CH:12]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 66894484HCID 66894484, compound

Product 1

HCID 66894718HCID 66894718, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

In a flask was placed (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4,4-difluoro-pentanoic acid methyl ester (139 mg, 0.39 mmol) in a 1:1 solution of tetrahydrofuran:water (8 mL) which was treated with lithium hydroxide monohydrate (35 mg, 0.78 mmol) and stirred for 1.5 h at 25° C. After such time, the mixture was concentrated in vacuo to remove the tetrahydrofuran and partioned between 1N aqueous hydrochloric acid (10 mL) and ethyl acetate (10 mL). The organic layer was separated, dried over sodium sulfate and concentrated in vacuo to afford (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4,4-difluoro-pentanoic acid (130 mg, 96%) as a light amber foam: HR-ES-MS m/z calculated for C15H14NO4ClF2 [M+H]+ 346.0652, observed 346.0652.

Workup

  1. customIn a flask was placed
  2. concentrationAfter such time, the mixture was concentrated in vacuo
  3. customto remove the tetrahydrofuran
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a5b97f4256554ee497934c1d57ee689e
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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