Lithium hydroxide, monohydrate → HCID 46180798, compound

HRID 2362225Notes

Reaction equation

HRID 2362225 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[CH:15][CH:14]=[C:13]2[CH2:25][CH2:26][C:27]([O:29]CC)=[O:28])=[C:8]([CH3:32])[CH:7]=1.O.[OH-].[Li+]>C1COCC1.O>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[CH:15][CH:14]=[C:13]2[CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[C:8]([CH3:32])[CH:7]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67178681HCID 67178681, compound

Product 1

HCID 46180798HCID 46180798, compoundYield 82%

Reagents, catalysts & solvents 1

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

Procedure

To a solution of ethyl 3-(1-(4-(1H-imidazol-2-yl)-2-methylphenyl)-5-(4-methoxyphenyl)-1H-pyrrol-2-yl)propanoate (100 mg, 0.233 mmol) in THF/H2O (v/v=1/1, 2 mL) was added lithium hydroxide monohydrate (15 mg, 0.350 mmol). The solution was stirred at room temperature overnight. THF was removed under reduced pressure and the resulting aqueous solution was acidified with 10% hydrochloric acid to pH=6.0. The resulting precipitate was isolated by centrifuge, rinsed with water, dried under reduced pressure to afford 3-(1-(4-(1H-imidazol-2-yl)-2-methylphenyl)-5-(4-methoxyphenyl)-1H-pyrrol-2-yl)propanoic acid as a brown powder (76 mg, 82%).

Workup

  1. customTHF was removed under reduced pressure
  2. customThe resulting precipitate was isolated by centrifuge
  3. washrinsed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-e0c730ffc8b443b2ae2e38bc375cda27
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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