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

HRID 896272Notes

Reaction equation

HRID 896272 reaction equation
C[O:2][C:3](=[O:38])[CH:4](NC([C@H]1CSCN1C(=O)C)=O)[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:38])=[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 695642522-(((S)-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

Product 1

HCID 865920993-((3-Methyl-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carbonyl)amino)propionic acidYield 76%

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 176 mg (0.32 mmol) of 2-(((S)-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 130 mg of 2-(3-acetylthiazolidine-4-carbonyl)amino)-3-((3-methyl-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carbonyl)amino)propionic acid (yield: 76%).

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-dd47bbce585a4244a4c59bb6e891fa66
Source dataset
uspto-grants-2005_07
Patent number
US06919349B2

Reaction notes

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