Sodium Hydroxide → 2-(4-Bromo-phenyl)-3-(3-diethylamino-pyrrolidin-1-yl)-propionic acid

HRID 220192Notes

Reaction equation

HRID 220192 reaction equation
C([O:3][C:4](=[O:24])[CH:5]([C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=1)[CH2:6][N:7]1[CH2:11][CH2:10][CH:9]([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[CH2:8]1)C.[OH-].[Na+]>CO>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([CH:5]([CH2:6][N:7]2[CH2:11][CH2:10][CH:9]([N:12]([CH2:13][CH3:14])[CH2:15][CH3:16])[CH2:8]2)[C:4]([OH:24])=[O:3])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 592383052-(4-Bromo-phenyl)-3-(3-diethylamino-pyrrolidin-1-yl)-propionic acid ethyl ester

Product 1

HCID 592382652-(4-Bromo-phenyl)-3-(3-diethylamino-pyrrolidin-1-yl)-propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(4-bromo-phenyl)-3-(3-diethylamino-pyrrolidin-1-yl)-propionic acid ethyl ester (639 mg, 1.6 mmol) in MeOH (4 mL) was added aq. NaOH (2N, 8 mmol). The solution was stirred at 40 degrees Celsius for 2 h, then concentrated in vacuo. The residue was dissolved in water and neutralized with 2N HCl to pH 5-6 at 0 degrees Celsius. Then the mixture was evaporated to dryness under reduced pressure to obtain a white solid product without further purification. MS: calc'd 369 (MH+), exp 369 (MH+).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water and neutralized with 2N HCl to pH 5-6 at 0 degrees Celsius
  3. customThen the mixture was evaporated to dryness under reduced pressure
  4. customto obtain a white solid product
  5. customwithout further purification

Sources & evidence

ORD record
ord-0aca52be4e514db1bc76e1028c8a7f92
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

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