Water → HCID 66895110, compound

HRID 19179Notes

Reaction equation

HRID 19179 reaction equation
C([O:3][C:4](=[O:28])[CH:5]([N:13]1[CH2:17][C:16]([O:18][C:19]2[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:20]=2[F:26])=[CH:15][C:14]1=[O:27])[CH2:6][C:7]1([F:12])[CH2:11][CH2:10][CH2:9][CH2:8]1)C.O.[OH-].[Li+].O>O1CCCC1.O>[F:26][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([F:25])[C:19]=1[O:18][C:16]1[CH2:17][N:13]([CH:5]([CH2:6][C:7]2([F:12])[CH2:8][CH2:9][CH2:10][CH2:11]2)[C:4]([OH:28])=[O:3])[C:14](=[O:27])[CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 66894898HCID 66894898, compound

Product 1

HCID 66895110HCID 66895110, compoundYield 88%

Reagents, catalysts & solvents 1

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

Procedure

To a solution of 2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-3-(1-fluoro-cyclopentyl)-propionic acid ethyl ester (0.440 g, 1.11 mol) in tetrahydrofuran:water (1:1, 10 mL) was added lithium hydroxide monohydrate (0.140 g 3.34 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 2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-3-(1-fluoro-cyclopentyl)-propionic acid, (0.358 g, 88%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.64 (br. s., 8H), 2.34 (dd, J=22.6, 6.9 Hz, 2H), 4.23 (d, J=18.4 Hz, 1H), 4.31 (d, J=18.4 Hz, 1H), 4.84 (t, J=6.9 Hz, 1H), 5.05 (s, 1H), 7.26-7.55 (m, 3H), 13.05 (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-d14ce779baaa4799afcba743ecb1eb61
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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