Hydrochloric Acid → 3-(2-{[(Tert-butoxy)carbonyl]amino}ethyl)benzoic acid
Reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9]C)=[O:8].[O:14](C(OC(C)(C)C)=O)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=O.Cl.[Na+].[Cl-]>[OH-].[Na+].O1CCOCC1>[C:18]([O:17][C:15]([NH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([OH:9])=[O:8])=[O:14])([CH3:21])([CH3:20])[CH3:19]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 22 °C
Procedure
To a solution of 1.90 g (10.6 mmol) of methyl 3-(2-aminoethyl)benzoate in 106 mL of 1 N NaOH and 50 mL of dioxane was added 3.47 g (15.9 mmol) of BOC2O in 10 mL of dioxane at 22° C. The solution was stirred for 2 h at 22° C. and then acidified to pH 2 by addition of 1 N HCl. The aqueous/organic mixture was saturated by stirring with solid NaCl and then extracted with DCM (5×100 mL). The combined organic extracts were dried (Na2SO4) and evaporated to give 3-(2-(tert-butoxycarbonylamino)ethyl)benzoic acid as a foamy white solid which was used subsequently without purification.
Workup
- extractionextracted with DCM (5×100 mL)
- dry with materialThe combined organic extracts were dried (Na2SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-3a26f9166bcb4a27a5ad6ac9bbacd763
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09227918B2
Reaction notes
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