Lithium Hydroxide → 3-(4-{1-[3-(2,4-Difluoro-phenyl)-1-heptyl-ureidomethyl]-cyclopropyl}-phenyl)-2-ethoxy-propionic acid

HRID 47800Notes

Reaction equation

HRID 47800 reaction equation
C[O:2][C:3](=[O:38])[CH:4]([O:35][CH2:36][CH3:37])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([CH2:15][N:16]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=3[F:27])=[O:18])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.[Li+].[OH-]>O1CCCC1>[F:27][C:21]1[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:20]=1[NH:19][C:17](=[O:18])[N:16]([CH2:15][C:12]1([C:9]2[CH:8]=[CH:7][C:6]([CH2:5][CH:4]([O:35][CH2:36][CH3:37])[C:3]([OH:38])=[O:2])=[CH:11][CH:10]=2)[CH2:13][CH2:14]1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 698844973-(4-{1-[3-(2,4-Difluoro-phenyl)-1-heptyl-ureidomethyl]-cyclopropyl}-phenyl)-2-ethoxy-propionic acid methyl ester

Product 1

HCID 234312253-(4-{1-[3-(2,4-Difluoro-phenyl)-1-heptyl-ureidomethyl]-cyclopropyl}-phenyl)-2-ethoxy-propionic acidYield 61.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(4-{1-[3-(2,4-difluoro-phenyl)-1-heptyl-ureidomethyl]-cyclopropyl}-phenyl)-2-ethoxy-propionic acid methyl ester (50 mg, 0.094 mmol) and 1 M LiOH (0.283 mmol, 0.283 mL) in tetrahydrofuran (1 mL) was allowed to stir at room temperature for 18 hours. 2 N HCL was then 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 2 M HCl (2×), dried over anhydrous sodium sulfate, and concentrated to give 3-(4-{1-[3-(2,4-difluoro-phenyl)-1-heptyl-ureidomethyl]-cyclopropyl}-phenyl)-2-ethoxy-propionic acid as a clear oil (30 mg, 61%).

Workup

  1. addition2 N HCL was then 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 2 M HCl (2×)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dbcca62de3a34df380ae732dc4c03b13
Source dataset
uspto-grants-2004_03
Patent number
US06699904B2

Reaction notes

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