Sodium Hydroxide → {4-[((3S)-3-Methyl-4-{[(phenylmethyl)oxy]carbonyl}-1-piperazinyl)methyl]phenyl}acetic Acid

HRID 43342Notes

Reaction equation

HRID 43342 reaction equation
[CH3:1][C@@H:2]1[N:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:6][CH2:5][N:4]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH:25](C(OCC)=O)[C:26]([O:28]CC)=[O:27])=[CH:21][CH:20]=2)[CH2:3]1.[OH-].[Na+]>O1CCOCC1>[CH3:1][C@@H:2]1[N:7]([C:8]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:9])[CH2:6][CH2:5][N:4]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][C:26]([OH:28])=[O:27])=[CH:23][CH:24]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 25223896Diethyl {4-[((3S)-3-methyl-4-{[(phenylmethyl)oxy]carbonyl}-1-piperazinyl)methyl]phenyl}propanedioate

Product 1

HCID 25223995{4-[((3S)-3-Methyl-4-{[(phenylmethyl)oxy]carbonyl}-1-piperazinyl)methyl]phenyl}acetic AcidYield 83.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of D7 (761 mg, 1.58 mmol), 2M NaOH solution (6 ml) and 1,4-dioxane (6 ml) was stirred at room temperature for 2 h. The solvents were removed and the residue dissolved in water and the pH adjusted to 4 with 2M HCl. The product was extracted with EtOAc and the combined extracts were dried and concentrated. The product was refluxed in toluene (˜20 ml) for 2 h and the solvent was evaporated to give the title compound as a yellow foam (505 mg). MS (ES): MH+ 383, (M−H)− 381.

Workup

  1. customThe solvents were removed
  2. dissolutionthe residue dissolved in water
  3. extractionThe product was extracted with EtOAc
  4. customthe combined extracts were dried
  5. concentrationconcentrated
  6. temperatureThe product was refluxed in toluene (˜20 ml) for 2 h
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-50de0c51beb44bd49768072aeb85b8a5
Source dataset
uspto-grants-2013_09
Patent number
US08536182B2

Reaction notes

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