Lithium hydroxide, monohydrate → 3-((8-(Tert-butoxycarbonyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

HRID 2362872Notes

Reaction equation

HRID 2362872 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:33]=[CH:34][CH:35]=1)[CH2:8][N:9]1[C:13](=[O:14])[C:12]2([CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[N:11]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:10]1)=[O:4].O.[OH-].[Li+]>CO.O>[C:23]([O:22][C:20]([N:17]1[CH2:18][CH2:19][C:12]2([N:11]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:10][N:9]([CH2:8][C:7]3[CH:6]=[C:5]([CH:35]=[CH:34][CH:33]=3)[C:3]([OH:4])=[O:2])[C:13]2=[O:14])[CH2:15][CH2:16]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66652862Tert-butyl 3-(3-(methoxycarbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 666520763-((8-(Tert-butoxycarbonyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acidYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of tert-Butyl 3-(3-(methoxycarbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (2 g, 4.17 mmol) in methanol (28 mL) was added lithium hydroxide monohydrate (0.35 g, 8.34 mmol) in water (14 mL). After stirring at room temperature for 18 h, the reaction mixture was concentrated in vacuo, acidified with dilute citric acid, extracted with dichloromethane. The organic extracts were washed with brine, dried over MgSO4, filtered and concentrated to obtain 3-((8-(tert-butoxycarbonyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid (1.88 g, 97%).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. extractionextracted with dichloromethane
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6fb5f7a1099f437fb0a6c88e1d99ffc8
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

Loading…