Hydrochloric Acid → 2-[(4-{3-[(2,4-Difluorobenzyl)(propyl)amino]-3-oxopropyl}phenoxy)methyl]benzoic acid

HRID 899895Notes

Reaction equation

HRID 899895 reaction equation
[F:1][C:2]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:3]=1[CH2:4][N:5]([CH2:28][CH2:29][CH3:30])[C:6](=[O:27])[CH2:7][CH2:8][C:9]1[CH:26]=[CH:25][C:12]([O:13][CH2:14][C:15]2[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=2[C:17]([O:19]C)=[O:18])=[CH:11][CH:10]=1.[OH-].[Li+].Cl>C1COCC1.O>[F:1][C:2]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:3]=1[CH2:4][N:5]([CH2:28][CH2:29][CH3:30])[C:6](=[O:27])[CH2:7][CH2:8][C:9]1[CH:26]=[CH:25][C:12]([O:13][CH2:14][C:15]2[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=2[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69179959Methyl 2-[(4-{3-[(2,4-difluorobenzyl)(propyl)amino]-3-oxopropyl}phenoxy)methyl]benzoate

Product 1

HCID 100732762-[(4-{3-[(2,4-Difluorobenzyl)(propyl)amino]-3-oxopropyl}phenoxy)methyl]benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-[(4-{3-[(2,4-difluorobenzyl)(propyl)amino]-3-oxopropyl}phenoxy)methyl]benzoate (0.184 g, 0.382 mmol) and lithium hydroxide (0.018 g, 0.76 mmol) in THF (2 ml) and water (2 ml) was heated at 150 degrees for 7 minutes. The mixture was diluted with water, acidified with hydrochloric acid and extracted with methylene chloride. The combined extracts were dried with magnesium sulfate and evaporated to give 2-[(4-{3-[(2,4-difluorobenzyl)(propyl)amino]-3-oxopropyl}phenoxy)methyl]benzoic acid.

Workup

  1. temperaturewas heated at 150 degrees for 7 minutes
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined extracts were dried with magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-67032068e3874abc96b04201090fdf6b
Source dataset
uspto-grants-2008_04
Patent number
US07355069B2

Reaction notes

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