Lithium hydroxide, monohydrate → HCID 58305674, compound

HRID 2362233Notes

Reaction equation

HRID 2362233 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=3)=[CH:13][CH:12]=[C:11]2[CH2:25][CH2:26][C:27]([O:29]CC)=[O:28])=[C:6]([CH3:32])[CH:5]=1)(=[O:3])[NH2:2].O.[OH-].[Li+]>C1COCC1.O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:22])=[O:23])=[CH:17][CH:16]=3)=[CH:13][CH:12]=[C:11]2[CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[C:6]([CH3:32])[CH:5]=1)(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58305754HCID 58305754, compound

Product 1

HCID 58305674HCID 58305674, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of ethyl 3-(1-(4-carbamoyl-2-methylphenyl)-5-(4-(methylsulfonyl)phenyl)-1H-pyrrol-2-yl)propanoate (28C) (100 mg, 0.22 mmol) in THF/H2O (v/v=1/1, 1 mL) was added lithium hydroxide monohydrate (18 mg, 0.44 mmol) and stirred overnight at room temperature. THF was evaporated in vacuum and the resulting aqueous solution was acidified with 10% hydrochloric acid to pH=4.0. The resulting precipitate was separated by centrifuge, rinsed with distilled water and purified by prep-HPLC to afford 3-(1-(4-carbamoyl-2-methylphenyl)-5-(4-(methylsulfonyl)phenyl)-1H-pyrrol-2-yl)propanoic acid (28D) as a light green solid (30 mg, 32%).

Workup

  1. customTHF was evaporated in vacuum
  2. customThe resulting precipitate was separated by centrifuge
  3. washrinsed with distilled water
  4. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-cc59663a210b42aab22eea5b295871d0
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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