Methanol → 4-(2-(2-((2R,5S)-4-(4-fluorobenzyl)-2,5-dimethylpiperazin-1-yl)-2-oxoethoxy)-5-chlorophenyl)-4-oxobutanoic acid

HRID 11623Notes

Reaction equation

HRID 11623 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[O:16][CH2:17][C:18]([N:20]1[CH2:25][C@H:24]([CH3:26])[N:23]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[CH2:22][C@H:21]1[CH3:35])=[O:19])=[O:8])C.O1CCCC1.CO.O.[OH-].[Li+]>O>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]([O:16][CH2:17][C:18]([N:20]2[CH2:25][C@H:24]([CH3:26])[N:23]([CH2:27][C:28]3[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=3)[CH2:22][C@H:21]2[CH3:35])=[O:19])=[C:9]([C:7](=[O:8])[CH2:6][CH2:5][C:4]([OH:36])=[O:3])[CH:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 684473824-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-4-oxo-butyric Acid Ethyl Ester

Product 1

HCID 444315294-(2-(2-((2R,5S)-4-(4-fluorobenzyl)-2,5-dimethylpiperazin-1-yl)-2-oxoethoxy)-5-chlorophenyl)-4-oxobutanoic acidYield 91.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-4-oxo-butyric acid ethyl ester (0.082 g, 0.16 mmol) in 2:2:1 tetrahydrofuran:methanol:water(1.5 mL) was added lithium hydroxide monohydrate (0.34 g, 0.79 mmol). The resulting solution was stirred 12 hours at ambient temperature, then concentrated in vacuo. The crude product was dissolved in ethyl acetate and washed with 1 M hydrochloric acid. The organics were dried over magnesium sulfate, filtered and concentrated in vacuo to give the title compound (0.072 g, LRMS: 489.4, 491.4).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe crude product was dissolved in ethyl acetate
  3. washwashed with 1 M hydrochloric acid
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a03833925d5e4fcc95b698c04ab760a1
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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