Lithium hydroxide, monohydrate → HCID 66893599, compound

HRID 19112Notes

Reaction equation

HRID 19112 reaction equation
C[O:2][C:3](=[O:26])[C@@H:4]([N:9]1[CH2:13][C:12]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH3:23])[C:16]=2[F:24])=[CH:11][C:10]1=[O:25])[CH2:5][CH:6]([CH3:8])[CH3:7].O.[OH-].[Li+]>O1CCCC1>[CH2:22]([O:21][C:17]1[C:16]([F:24])=[C:15]([CH:20]=[CH:19][CH:18]=1)[O:14][C:12]1[CH2:13][N:9]([C@@H:4]([CH2:5][CH:6]([CH3:8])[CH3:7])[C:3]([OH:26])=[O:2])[C:10](=[O:25])[CH:11]=1)[CH3:23]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66894996HCID 66894996, compound

Product 1

HCID 66893599HCID 66893599, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution containing (S)-2-[4-(3-ethoxy-2-fluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid methyl ester (2.40 g, 0.007 mol) in tetrahydrofuran (40 mL) was treated with an aqueous solution of lithium hydroxide monohydrate (0.5N, 30 mL, 0.015 mol). The mixture was stirred at room temperature for 2H, and the solvents evaporated. The residue was dissolved in water and washed with diethyl ether, and the diethyl ether layer discarded. The aqueous phase was acidified with dilute hydrochloric acid (pH <2), and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to afford (S)-2-[4-(3-ethoxy-2-fluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid (2.00 g, 87%) as a white solid after triturating with diethyl ether.

Workup

  1. customthe solvents evaporated
  2. dissolutionThe residue was dissolved in water
  3. washwashed with diethyl ether
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b47d270044e74504ac458dbb8647fdce
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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