Lithium Hydroxide → 4-[(4E)-3-(4-Carboxybenzyl)-5-{2-[3-(2-oxopyrrolidin-1-yl)propoxy]phenyl}pent-4-en-1-yl]-benzoic acid

HRID 1512223Notes

Reaction equation

HRID 1512223 reaction equation
[OH-].[Li+].C[O:4][C:5]([C:7]1[CH:44]=[CH:43][C:10]([CH2:11][CH:12](/[CH:25]=[CH:26]/[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH2:34][CH2:35][CH2:36][N:37]2[CH2:41][CH2:40][CH2:39][C:38]2=[O:42])[CH2:13][CH2:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)=[O:6]>C1COCC1.O>[C:5]([C:7]1[CH:8]=[CH:9][C:10]([CH2:11][CH:12](/[CH:25]=[CH:26]/[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH2:34][CH2:35][CH2:36][N:37]2[CH2:41][CH2:40][CH2:39][C:38]2=[O:42])[CH2:13][CH2:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=2)=[CH:43][CH:44]=1)([OH:6])=[O:4]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59437424Methyl 4-[(4E)-3-[4-(methoxycarbonyl)benzyl]-5-{2-[3-(2-oxopyrrolidin-1-yl)propoxy]phenyl}pent-4-en-1-yl]benzoate

Product 1

HCID 249703434-[(4E)-3-(4-Carboxybenzyl)-5-{2-[3-(2-oxopyrrolidin-1-yl)propoxy]phenyl}pent-4-en-1-yl]-benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

492 mg (20.5 mmol) of lithium hydroxide are added to a solution of 3.90 g (6.8 mmol) of methyl 4-[(4E)-3-[4-(methoxycarbonyl)benzyl]-5-{2-[3-(2-oxopyrrolidin-1-yl)propoxy]phenyl}pent-4-en-1-yl]benzoate (Example 21A) in 20 ml of THF and 20 ml of water, and the mixture is stirred at 50° C. for 12 h. The mixture is then cooled and extracted three times with ethyl acetate. The aqueous phase is then adjusted to pH 2 using 1 M hydrochloric acid and extracted three times with ethyl acetate. The latter organic phases are combined, washed with water and saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent is removed to dryness. This gives 2.75 g (content 98%, 4.98 mmol, 73% of theory) of the title compound as a colorless solid.

Workup

  1. temperatureThe mixture is then cooled
  2. extractionextracted three times with ethyl acetate
  3. extractionextracted three times with ethyl acetate
  4. washwashed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent is removed to dryness

Sources & evidence

ORD record
ord-8372900194774e2d850ef0f169cca451
Source dataset
uspto-grants-2012_07
Patent number
US08217063B2

Reaction notes

Loading…