Hydrochloric Acid → 6-[5-Ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinamido]hexanoic acid

HRID 2187047Notes

Reaction equation

HRID 2187047 reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([C:21]2[NH:22][C:23](=[O:30])[C:24]([CH:27]([CH3:29])[CH3:28])([CH3:26])[N:25]=2)=[C:7]([CH:20]=1)[C:8]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]C)=[O:17])=[O:9])[CH3:2].[OH-].[Na+].Cl>O1CCCC1>[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([C:21]2[NH:22][C:23](=[O:30])[C:24]([CH:27]([CH3:29])[CH3:28])([CH3:26])[N:25]=2)=[C:7]([CH:20]=1)[C:8]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:9])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22450188Methyl 6-[5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinamido]hexanoate

Product 1

HCID 189772396-[5-Ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinamido]hexanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of methyl 6-[5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinamido]-hexanoate (5.14 g, 12.35 mmol) in tetrahydrofuran is treated with 2N sodium hydroxide (15 mL). The resulting mixture is stirred at room temperature for 24 hours. After this period, the reaction mixture is concentrated in vacuo to obtain a residue. The residue is cooled with an ice bath and acidified with concentrated hydrochloric acid. The resulting precipitate is isolated by vacuum filtration and washed with water to give the title product as a white solid, mp 76-81° C.

Workup

  1. waitAfter this period
  2. concentrationthe reaction mixture is concentrated in vacuo
  3. customto obtain a residue
  4. temperatureThe residue is cooled with an ice bath
  5. customThe resulting precipitate is isolated by vacuum filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-3733f18bce244dbbbff98fdd5be61349
Source dataset
uspto-grants-2002_06
Patent number
US06407217B1

Reaction notes

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