Lithium Hydroxide → HCID 56679373, compound

HRID 2362227Notes

Reaction equation

HRID 2362227 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][CH2:6][C:7]1[N:8]([C:23]2[CH:28]=[CH:27][C:26]([C:29](=[O:31])[NH2:30])=[CH:25][C:24]=2[CH3:32])[C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[N:20][NH:21][N:22]=3)=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)C.[OH-].[Li+]>CO.C1COCC1>[N:22]1[NH:21][N:20]=[N:19][C:18]=1[C:15]1[CH:16]=[CH:17][C:12]([C:9]2[N:8]([C:23]3[CH:28]=[CH:27][C:26]([C:29](=[O:31])[NH2:30])=[CH:25][C:24]=3[CH3:32])[C:7]([CH2:6][CH2:5][C:4]([OH:33])=[O:3])=[CH:11][CH:10]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58305709HCID 58305709, compound

Product 1

HCID 56679373HCID 56679373, compoundYield 102.9%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To 3-{1-(4-carbamoyl-2-methyl-phenyl)-5-[4-(2H-tetrazol-5-yl)-phenyl]-1H-pyrrol-2-yl}-propionic acid ethyl ester (26B) (16 mg, 0.035 mmol.) in 1:1 MeOH/THF (1.0 mL) was added aq. 1.0 N lithium hydroxide (2 eq). The reaction mixture was allowed to stir at rt for 16 h. The reaction mixture was poured into 10 mL ice-water solution which was extracted with diethyl ether. The aqueous layer was acidified with aq HCl (2 N) to pH=2, and then was extracted with diethyl ether. The combined organic layers were dried over Na2SO4. The solvent was removed under vacuum to yield the desired target 3-(5-(4-(2H-tetrazol-5-yl)phenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl)propanoic acid (26C) (15 mg, 95%).

Workup

  1. extractionwas extracted with diethyl ether
  2. extractionwas extracted with diethyl ether
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-e43d695bba734e829c20ae3e6d135e99
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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