Lithium Hydroxide → HCID 178440185, compound

HRID 1197603Notes

Reaction equation

HRID 1197603 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[CH:10]=[CH:9][N:8]([C:11]2[N:12]=[C:13]([CH2:38][CH2:39][CH3:40])[N:14]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]4[NH:37][N:36]=[N:35][N:34]=4)=[CH:23][CH:22]=3)[C:15]=2[C:16]([O:18]C)=[O:17])[CH:7]=1)([OH:3])=[O:2].[OH-].[Li+]>C(O)C.O>[C:1]([CH2:4][CH2:5][C:6]1[CH:10]=[CH:9][N:8]([C:11]2[N:12]=[C:13]([CH2:38][CH2:39][CH3:40])[N:14]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]4[NH:37][N:36]=[N:35][N:34]=4)=[CH:23][CH:22]=3)[C:15]=2[C:16]([OH:18])=[O:17])[CH:7]=1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 178440184HCID 178440184, compound

Product 1

HCID 178440185HCID 178440185, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of methyl 4-(3-carboxyethyl-1H-pyrrol-1-yl)-2-propyl-1-[(2'-(1H-tetrazol 5-yl)biphen-4-yl)methyl]-1H-imidazole-5-carboxylate (Example 73, 0.2 g) in ethanol (2.5 mL) and water (1.25 mL) was treated with lithium hydroxide (0.17 g) ant the reaction mixture stirred a room temperature for 3 days. The reaction mixture was diluted with water, extracted with ether, and the aqueous layer acidified to pH 2 with 1N HCl. The cloudy solution was extracted with ether and the combined organic layers dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue taken-up in ethyl acetate. Petroleum ether was added dropwise to precipitate the product which was collected by filtration to yield 0.11 g of the title compound 4-(3-carboxyethyl-1H-pyrrol-1-yl)-2-propyl-1-[(2'-(1H-tetrazol-5-yl)biphen-4-yl)methyl]-1H-imidazole-5-carboxylic acid. MS (CI, CH4 +NH4) 410 (M-CO2H, --CO2Et).

Workup

  1. extractionextracted with ether
  2. extractionThe cloudy solution was extracted with ether
  3. dry with materialthe combined organic layers dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. additionPetroleum ether was added dropwise
  6. customto precipitate the product which
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-2e32f550984f42c68bd98536cf53a09b
Source dataset
uspto-grants-1994_01
Patent number
US05276048

Reaction notes

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