Sodium Hydroxide → HCID 46181959, compound

HRID 2362228Notes

Reaction equation

HRID 2362228 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])N)=[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-:34].[Na+]>CO>[N:19]1[NH:20][N:21]=[N:22][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]([OH:34])=[O:31])=[CH:25][C:24]=3[CH3:32])[C:7]([CH2:6][CH2:5][C:4]([OH:3])=[O:33])=[CH:11][CH:10]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58305709HCID 58305709, compound

Product 1

HCID 46181959HCID 46181959, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 (25 mg, 0.055 mmol.) in MeOH (2 mL) was added aq. sodium hydroxide (15%, 0.5 mL). The reaction mixture was allowed to stir at rt for 16 h. The reaction mixture was poured into 20 mL ice-water solution which was extracted with diethyl ether (2×10 mL). The aqueous layer was acidified with aq HCl (2 N) to pH=1-2, and then was extracted with diethyl ether (6×10 mL). The combined organic layers were dried over Na2SO4. The solvent was removed under vacuum to yield the desired target 4-(2-(4-(2H-tetrazol-5-yl)phenyl)-5-(2-carboxyethyl)-1H-pyrrol-1-yl)-3-methylbenzoic acid (26D) (15 mg, 65%).

Workup

  1. extractionwas extracted with diethyl ether (2×10 mL)
  2. extractionwas extracted with diethyl ether (6×10 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-d4ae1c50ca244290b3a9e28280becbb6
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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