Water → (S)-2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-pentanoic acid

HRID 19173Notes

Reaction equation

HRID 19173 reaction equation
C[O:2][C:3](=[O:23])[C@@H:4]([N:8]1[CH2:12][C:11]([O:13][C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=2[F:21])=[CH:10][C:9]1=[O:22])[CH2:5][CH2:6][CH3:7].O.[OH-].[Li+].O>O1CCCC1.O>[F:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([F:20])[C:14]=1[O:13][C:11]1[CH2:12][N:8]([C@@H:4]([CH2:5][CH2:6][CH3:7])[C:3]([OH:23])=[O:2])[C:9](=[O:22])[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 66894831HCID 66894831, compound

Product 1

HCID 66895372(S)-2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-pentanoic acidYield 87%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of (S)-2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-pentanoic acid methyl ester (0.108 g, 0.33 mol) in tetrahydrofuran:water (1:1, 8 mL) was added lithium hydroxide monohydrate (0.042 g 1.00 mmol). The mixture was stirred at room temperature for 2 h. The reaction mixture was poured into water and washed with diethyl ether and the diethyl ether layer discarded. The aqueous phase was acidified with 1N aqueous hydrochloric acid (pH <2), and extracted with ethyl acetate (2×30 mL). The combined ethyl acetate layers were dried over magnesium sulfate, filtered and concentrated to afford (S)-2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-pentanoic acid, (0.086 g, 87%), as an off-white solid: LR-ES-MS m/z calculated for C15H15F2NO4 [M+H]+ 312, observed 312.

Workup

  1. washwashed with diethyl ether
  2. extractionextracted with ethyl acetate (2×30 mL)
  3. dry with materialThe combined ethyl acetate layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-36224a4a596d4fb0b477611d62a22027
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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