Water → HCID 66894798, compound

HRID 19175Notes

Reaction equation

HRID 19175 reaction equation
C[O:2][C:3](=[O:22])[C@@H:4]([N:7]1[CH2:11][C:10]([O:12][C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=2[F:20])=[CH:9][C:8]1=[O:21])[CH2:5][CH3:6].O.[OH-].[Li+].O>O1CCCC1.O>[F:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([F:19])[C:13]=1[O:12][C:10]1[CH2:11][N:7]([C@@H:4]([CH2:5][CH3:6])[C:3]([OH:22])=[O:2])[C:8](=[O:21])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 66893702HCID 66893702, compound

Product 1

HCID 66894798HCID 66894798, compoundYield 83%

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]-butyric acid methyl ester (0.119 g, 0.38 mol) in tetrahydrofuran:water (1:1, 8 mL) was added lithium hydroxide monohydrate (0.050 g 1.19 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 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]-butyric acid (0.090 g, 83%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.87 (t, J=7.4 Hz, 3H), 1.60-2.06 (m, 2H), 4.23 (d, J=18.7 Hz, 1H), 4.31 (d, J=18.7 Hz, 1H), 4.43 (dd, J=10.7, 5.0 Hz, 1H), 5.05 (s, 1H), 7.21-7.54 (m, 3H), 12.94 (br. s., 1H).

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-d2526e405b094e2499bfa336a1998568
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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