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Diethyl Ether → 2-(2-((2R,5S)-4-(4-fluorobenzyl)-2,5-dimethylpiperazin-1-yl)-2-oxoethoxy)-5-chlorobenzoic acid

HRID 480181
Notes
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Reaction equation

HRID 480181 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[O:11][CH2:12][C:13]([N:15]1[CH2:20][C@H:19]([CH3:21])[N:18]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:17][C@H:16]1[CH3:30])=[O:14].O.[OH-].[Li+].C(OCC)C>O1CCCC1.CO.O.ClCCl>[Cl:10][C:8]1[CH:7]=[CH:6][C:5]([O:11][CH2:12][C:13]([N:15]2[CH2:20][C@H:19]([CH3:21])[N:18]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)[CH2:17][C@H:16]2[CH3:30])=[O:14])=[C:4]([CH:9]=1)[C:3]([OH:31])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 3283Diethyl EtherHCID 168937Lithium hydroxide, monohydrateHCID 11487716rel-Methyl 5-chloro-2-[2-[(2R,5S)-4-[(4-fluorophenyl)methyl]-2,5-dimethyl-1-piperazinyl]-2-oxoethoxy]benzoate

Product 1

HCID 111664342-(2-((2R,5S)-4-(4-fluorobenzyl)-2,5-dimethylpiperazin-1-yl)-2-oxoethoxy)-5-chlorobenzoic acidYield 35%

Reagents, catalysts & solvents 4

HCID 887
Methanol
Solvent
HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R, 5S)-5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzoic acid methyl ester (4.12 g, 9.18 mmol) in tetrahydrofuran (10 ml), methanol (10 ml) and water (4 ml) was added lithium hydroxide monohydrate (1.93 g, 45.9 mmol). The resulting mixture was stirred overnight at ambient temperature. The reaction was then concentrated, diluted with 1N hydrochloric acid and extracted with dichloromethane (2×). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated to give a white foam. Triteration in dichloromethane and diethyl ether gave the title compound (1.38 g, 35% yield).

Workup

  1. concentrationThe reaction was then concentrated
  2. additiondiluted with 1N hydrochloric acid
  3. extractionextracted with dichloromethane (2×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a white foam

Sources & evidence

ORD record
ord-18c818dae80843adad35ee74a9ee10be
Source dataset
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06649611B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes