Lithium hydroxide, monohydrate → HCID 66899051, compound

HRID 19399Notes

Reaction equation

HRID 19399 reaction equation
C[O:2][C:3](=[O:30])[C@@H:4]([N:9]1[CH2:13][C:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C@H:22]3[CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23]3)=[CH:17][CH:16]=2)=[CH:11][C:10]1=[O:29])[CH2:5][CH:6]([CH3:8])[CH3:7].O.[OH-].[Li+]>O1CCCC1.O>[CH3:28][C:24]1([CH3:27])[O:23][C@@H:22]([CH2:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][C:12]3[CH2:13][N:9]([C@@H:4]([CH2:5][CH:6]([CH3:8])[CH3:7])[C:3]([OH:30])=[O:2])[C:10](=[O:29])[CH:11]=3)=[CH:16][CH:17]=2)[CH2:26][O:25]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66899367HCID 66899367, compound

Product 1

HCID 66899051HCID 66899051, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-2-{4-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenoxy]-2-oxo-2,5-dihydro-pyrrol-1-yl}-4-methyl-pentanoic acid methyl ester (0.198 g, 0.47 mmol) in tetrahydrofuran (5 mL) and water (1 mL) was treated with lithium hydroxide monohydrate (0.022 g 0.51 mmol) and stirred at room temperature for 1.5 h. The mixture was partitioned between ethyl acetate and water and the layers separated. The aqueous phase was acidified with 1N aqueous hydrochloric acid (pH=1) and extracted with ethyl acetate. The combined organic layers from extraction of the acidic aqueous layer were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was treated with dichloromethane/hexanes and the precipitate isolated by filtration to afford (S)-2-{4-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenoxy]-2-oxo-2,5-dihydro-pyrrol-1-yl}-4-methyl-pentanoic acid (148 mg, 77%), as a white solid.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customthe layers separated
  3. extractionextracted with ethyl acetate
  4. extractionThe combined organic layers from extraction of the acidic aqueous layer
  5. dry with materialwere dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. additionThe residue was treated with dichloromethane/hexanes
  9. customthe precipitate isolated by filtration

Sources & evidence

ORD record
ord-abf790df85d3460f9a32acb2b24d0eeb
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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