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Lithium Hydroxide → 4-{(3R)-3-[(4-{[(3,4-Dichlorophenyl)amino]carbonyl}piperazin-1-yl)methyl]piperidin-1-yl}butanoic acid

HRID 2371188
Notes
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Reaction equation

HRID 2371188 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][N:21]([CH2:25][CH2:26][CH2:27][C:28]([O:30]C)=[O:29])[CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[Li+]>O1CCCC1>[NH3:9].[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][N:21]([CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57656696methyl 4-{(3R)-3-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)methyl]piperidin-1-yl}butanoate

Product 2

HCID 222AmmoniaHCID 576566474-{(3R)-3-[(4-{[(3,4-Dichlorophenyl)amino]carbonyl}piperazin-1-yl)methyl]piperidin-1-yl}butanoic acidYield 154.6%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of methyl 4-{(3R)-3-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)methyl]piperidin-1-yl}butanoate (80 mg) in tetrahydrofuran (5 mL) was added 1M aqueous lithium hydroxide (1 mL). The mixture was stirred overnight at room temperature. The mixture was then loaded directly onto an SCX-2 column and eluted with methanol then 7M NH3 in methanol. The basic fraction was concentrated at reduced pressure and the residue was purified using reverse phase HPLC eluting with a mixture of 5-95% acetonitrile in water and then SCX-2 column eluting with methanol then 7M NH3 in methanol to give the title compound as a white solid (60 mg, 77%).

Workup

  1. washeluted with methanol
  2. concentrationThe basic fraction was concentrated at reduced pressure
  3. customthe residue was purified
  4. washeluting with a mixture of 5-95% acetonitrile in water
  5. washSCX-2 column eluting with methanol

Sources & evidence

ORD record
ord-41a15351811d4f1a9f08994ffa6488e8
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08710224B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes