Sodium Hydroxide → HCID 67411497, compound
Reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:22])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:8]([Br:21])[CH:7]=1>O.CO>[Br:21][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=1[CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:5]([OH:22])=[O:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a solution of the previous di_Boc protected benzylamine (290 g, 0.652 mol, 1.0 eq) in DCM (2.9 L) was added TFA (92.8 g, 0.813 mol, 1.25 eq) dropwise at 0° C., the resulting mixture was stirred at room temperature for 4 hrs. 0.5 M NaHCO3 was added to the mixture to adjust pH to 8. The reaction mixture was washed with water (3*500 ml), dried over MgSO4 and concentrated by rotavapor to give 3-bromo-4-(tert-butoxycarbonylamino-methyl)-benzoic acid methyl ester (210 g, 93.5% yield) as yellow oil. NaOH (48.8 g, 1.22 mol, 2.0 eq) in H2O (1.26 L) was added to a solution of 3-bromo-4-(tert-butoxycarbonylamino-methyl)-benzoic acid methyl ester (210 g, 0.61 mol, 1.0 eq) in MeOH (1.26 L). The reaction mixture was stirred at 50° C. for 2 hrs. The reaction was cooled to room temperature and concentrated to half volume. The residue was acidified to pH 5 by adding 1M HCl solution. The resulting solid was collected and dried to give the title intermediate (200 g, 99.4% yield) as white solid.
Workup
- temperatureThe reaction was cooled to room temperature
- concentrationconcentrated to half volume
- additionby adding 1M HCl solution
- customThe resulting solid was collected
- customdried
Sources & evidence
- ORD record
- ord-d037fa5dfa56462695424e6c27db79dc
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815873B2
Reaction notes
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