Hydrochloric Acid → 3-((3-Methyl-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carbonyl)amino)propionic acid

HRID 896274Notes

Reaction equation

HRID 896274 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][CH2:5][NH:6][C:7]([N:9]1[CH2:26][CH2:25][C:12]2([N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:15][N:14]([CH3:23])[C:13]2=[O:24])[CH2:11][CH2:10]1)=[O:8].Cl>O1CCCC1.[OH-].[Li+]>[CH3:23][N:14]1[C:13](=[O:24])[C:12]2([CH2:25][CH2:26][N:9]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:27])=[O:2])=[O:8])[CH2:10][CH2:11]2)[N:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:15]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 865921003-((3-Methyl-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carbonyl)amino)propionic acid methyl ester

Product 1

HCID 865920993-((3-Methyl-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carbonyl)amino)propionic acidYield 81%

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 171 mg (0.31 mmol) of 2-(3-acetylthiazolidin-4-carbonyl)amino)-3-((3-methyl-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carbonyl)amino)propionic acid methyl ester in 4 ml of tetrahydrofuran, 4 ml of 0.1M aqueous lithium hydroxide solution was added, and the resulting mixture was stirred overnight at room temperature. To the reaction mixture, 0.1M hydrochloric acid was added, and the resulting mixture was extracted with ethyl acetate. Organic phases were combined, washed with saturated saline, dried over anhydrous sodium sulfate, and concentrated. The residue was reprecipitated from ether/chloroform to obtain 135 mg of 2-(3-acetylthiazolidin-4-carbonyl)amino)-3-((3-methyl-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carbonyl)amino)propionic acid (yield: 81%).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washwashed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was reprecipitated from ether/chloroform

Sources & evidence

ORD record
ord-ee12ce56ba914e0ca3cd047eb8c34b2d
Source dataset
uspto-grants-2005_07
Patent number
US06919349B2

Reaction notes

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