Hydrochloric Acid → 2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]-2-[(2-methyl-5-tetrazolyl)methyl]acetic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@H:13]([CH2:18][C:19]2[N:20]=[N:21][N:22]([CH3:24])[N:23]=2)[C:14]([O:16]C)=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.O.[OH-].[Li+].Cl>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]([CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C@H:13]([CH2:18][C:19]2[N:20]=[N:21][N:22]([CH3:24])[N:23]=2)[C:14]([OH:16])=[O:15])(=[O:10])=[O:11])=[CH:7][CH:8]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Methyl 2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]-2-[(2-methyl-5-tetrazolyl)-methyl]acetate (1.0 g, 2.27 mmol) is dissolved in tetrahydrofuran (11.3 mL) and water (11.3 mL). To this solution is added lithium hydroxide hydrate (0.095 g, 2.27 mmol), and the reaction is stirred at room temperature for 2 hours. The reaction is then acidified to pH=~3 using 1N hydrochloric acid, and extracted well with ethyl acetate. The combined organic extracts are washed with brine, dried (Na2SO4), and the solvent is evaporated to provide 2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]-2-[(2-methyl-5-tetrazolyl)-methyl]acetic acid (0.96 g).
Workup
- extractionextracted well with ethyl acetate
- washThe combined organic extracts are washed with brine
- dry with materialdried (Na2SO4)
- customthe solvent is evaporated
Sources & evidence
- ORD record
- ord-3991f7aded7c495994d242833afaba51
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05552419
Reaction notes
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