Lithium hydroxide, monohydrate → HCID 66893940, compound

HRID 19147Notes

Reaction equation

HRID 19147 reaction equation
C[O:2][C:3](=[O:28])[C@@H:4]([N:9]1[CH2:13][C:12]([O:14][C:15]2[C:20]([F:21])=[CH:19][CH:18]=[C:17]([O:22][CH:23]([CH3:25])[CH3:24])[C:16]=2[F:26])=[CH:11][C:10]1=[O:27])[CH2:5][CH:6]([CH3:8])[CH3:7].O.[OH-].[Li+]>O1CCCC1>[F:26][C:16]1[C:17]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:18][CH:19]=[C:20]([F:21])[C:15]=1[O:14][C:12]1[CH2:13][N:9]([C@@H:4]([CH2:5][CH:6]([CH3:8])[CH3:7])[C:3]([OH:28])=[O:2])[C:10](=[O:27])[CH:11]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66894660HCID 66894660, compound

Product 1

HCID 66893940HCID 66893940, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution containing (S)-2-[4-(2,6-difluoro-3-isopropoxy-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid methyl ester (3.10 g, 0.008 mol) in tetrahydrofuran (35 mL) was treated with an aqueous solution of lithium hydroxide monohydrate (0.5N, 35 mL, 0.018 mol). The mixture was stirred at 20° C. 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-(2,6-difluoro-3-isopropoxy-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid (2.64 g, 88%) as a tan solid.

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-ec8bdb41852441309cd2c81b3e645126
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

Loading…