Lithium Hydroxide → HCID 46181265, compound

HRID 1188277Notes

Reaction equation

HRID 1188277 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][CH2:6][C:7]1[N:8]([C:20]2[S:21][CH:22]=[C:23]([C:25](=[O:27])[NH2:26])[N:24]=2)[C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)C.[Li+].[OH-]>CO.C1COCC1>[C:25]([C:23]1[N:24]=[C:20]([N:8]2[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[CH:10][CH:11]=[C:7]2[CH2:6][CH2:5][C:4]([OH:28])=[O:3])[S:21][CH:22]=1)(=[O:27])[NH2:26]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67175500HCID 67175500, compound

Product 1

HCID 46181265HCID 46181265, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To 3-[1-(4-Carbamoyl-thiazol-2-yl)-5-(4-methoxy-phenyl)-1H-pyrrol-2-yl]-propionic acid ethyl ester (0.15 mmol) in a 2:1 mixture of methanol/THF was added 2M LiOH (0.30 mmol). The reaction mixture was stirred for 24 hours. The solvent was removed in vacuo. The residue was diluted with water (2 mL) and extracted with ethyl ether. The pH of the aqueous layer was adjusted to 2 with 1N HCl. The resulting suspension was filtered; the solid was washed with water and dried to give the final compound. Yield: 36 mg, 69%.

Workup

  1. customThe solvent was removed in vacuo
  2. additionThe residue was diluted with water (2 mL)
  3. extractionextracted with ethyl ether
  4. filtrationThe resulting suspension was filtered
  5. washthe solid was washed with water
  6. customdried

Sources & evidence

ORD record
ord-82da78fd2c2440a496bd17e1ffa7e1fd
Source dataset
uspto-grants-2014_03
Patent number
US08673961B2

Reaction notes

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