Hydrochloric Acid → HCID 22128904, compound
Reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]2[O:24][CH2:25][C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4].[OH-].[Na+].Cl>CO>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][CH:11]([C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:3]([OH:4])=[O:2])[CH:12]([O:24][CH2:25][C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=2)[CH2:13]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 60 mg (0.13 mmol) of tert-butyl (3RS,4RS)-4-(3-methoxycarbonyl-phenyl)-3-naphthalen-2-ylmethoxy-piperidine-1-carboxylate (Example 26(e)] and 0.26 ml (0.26 mmol) of 1N sodium hydroxide solution in 2 ml of methanol was stirred at 30° C. for 18 hours. For the working-up, the reaction mixture was neutralized with 1N hydrochloric acid and extracted twice with 10 ml of methylene chloride each time. The organic phases were combined, dried over sodium sulphate and evaporated under reduced pressure. The residue was crystallized from a mixture of hexane and diethyl ether. There were obtained 45 mg (75% of theory) of (3RS,4RS)-3-(1-tert-butoxycarbonyl-3-naphthalen-2-ylmethoxy-piperidin-4-yl)-benzoic acid as colourless crystals; MS: 462 (M+H)+.
Workup
- extractionextracted twice with 10 ml of methylene chloride each time
- dry with materialdried over sodium sulphate
- customevaporated under reduced pressure
- customThe residue was crystallized from a mixture of hexane and diethyl ether
Sources & evidence
- ORD record
- ord-eb40de07a13240e3ac55ace60ab4bc21
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06051712
Reaction notes
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