Lithium Hydroxide → HCID 23431214, compound

HRID 47797Notes

Reaction equation

HRID 47797 reaction equation
C[O:2][C:3](=[O:36])[CH:4]([O:33][CH2:34][CH3:35])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][N:14]([C:22](=[O:32])[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[F:31])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:8][CH:7]=1.[Li+].[OH-]>O1CCCC1>[F:31][C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1[CH2:23][C:22]([N:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:13][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH:4]([O:33][CH2:34][CH3:35])[C:3]([OH:36])=[O:2])=[CH:7][CH:8]=1)=[O:32]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 121254603-[4-(2-{[(2,4-Difluoro-phenyl)-acetyl]-heptyl-amino}-ethyl)-phenyl]-2-ethoxy-propionic acid methyl ester

Product 1

HCID 23431214HCID 23431214, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[4-(2-{[(2,4-difluoro-phenyl)-acetyl]-heptyl-amino}-ethyl)-phenyl]-2-ethoxy-propionic acid methyl ester (35 mg, 0.07 mmol) and 1 M LiOH (0.208 mmol, 0.208 mL) in tetrahydrofuran (1 mL) was allowed to stir at room temperature for 78 hours. 2 N HCL was added until the solution had a pH<2. After dilution with twice its volume in water, the aqueous layer was extracted with diethyl ether (2×). The organic layers were combined, washed with 2M HCl (2×), dried over anhydrous sodium sulfate, and concentrated to give 3-[4-(2-{[(2,4-difluoro-phenyl)-acetyl]-heptyl-amino}-ethyl)-phenyl]-2-ethoxy-propionic acid as a clear oil (28.6 mg, 84%).

Workup

  1. addition2 N HCL was added until the solution
  2. extractionAfter dilution with twice its volume in water, the aqueous layer was extracted with diethyl ether (2×)
  3. washwashed with 2M HCl (2×)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8d73ba4e433b4c76a74d99cd4c897942
Source dataset
uspto-grants-2004_03
Patent number
US06699904B2

Reaction notes

Loading…