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CC(C)(CO)C(=O)NCC1=CC=CC=C1ClChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | N-[(2-chlorophenyl)methyl]-3-hydroxy-2,2-dimethylpropanamide |
|---|---|
| IUPAC Name | — |
| CAS Number | 171569-37-2 |
| Database ID | 59778447 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
N-[(2-chlorophenyl)methyl]-3-hydroxy-2,2-dimethylpropanamide (CAS 171569-37-2) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 59778447
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-286eae15c5ea4000a3e3b94d9c9c85e6Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-4d01cab0424b4e2fa0d75a847ac32313Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of N-(2-chlorobenzyl)-3-hydroxy-2,2-dimethylpropanamide (0.50 g, 2.07 mmol) in THF (5 mL) were added phthalimide (0.457 g, 3.10 mmol, 1.5 equiv.) and PPh3 (0.813 g, 3.10 mmol, 1.5 equiv.). DIAD (600 μL, 3.10 mmol, 1.5 equiv.) was added dropwise into the reaction mixture. The resulting mixture was stirred overnight. LC/MS indicated that starting material was consumed. The reaction mixture was concentrated. The resulting residue was purified on silica gel column a mixture of hexanes and ethyl acetate to give N-(2-chlorobenzyl)-3-(1,3-dioxoisoindolin-2-yl)-2,2-dimethylpropanamide (0.50 g, 65%). LRMS (M+H+) m/z 371.1. was consumed The reaction mixture was concentrated The resulting residue was purified on silica gel column a mixture of hexanes and ethyl acetate
Source ID: ord-6acabc4af0fd41d781bd72884f793398Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of methyl 3-hydroxy-2,2-dimethylpropanoate (1.0 g, 7.57 mmol) and 2-chlorobenzylamine (1.09 mL, 9.08 mmol, 1.2 equiv.) in toluene (10 mL) was added trimethylaluminum (2M in hexanes, 5.6 mL, 11.4 mmol, 1.5 equiv.). The reaction mixture was stirred at 80° C. for 2 hours. The reaction mixture was concentrated. The resulting residue was dissolved in EtOAc (100 mL). The organic layer was washed with saturated NaHCO3, dried over Na2SO4, and concentrated. The resulting residue was purified on silica gel column using a mixture of hexanes and ethyl acetate to give N-(2-chlorobenzyl)-3-hydroxy-2,2-dimethylpropanamide (1.55 g, 84%). LRMS (M+H+) m/z 242.1. The reaction mixture was concentrated The resulting residue was dissolved in EtOAc (100 mL) The organic layer was washed with saturated NaHCO3 dried over Na2SO4 concentrated The resulting residue was purified on silica gel column a mixture of hexanes and ethyl acetate
Source ID: ord-74d8738b1782456c9ad0e5214729b31eConditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of methyl 3-hydroxy-2,2-dimethylpropanoate (1.0 g, 7.57 mmol) and 2-chlorobenzylamine (1.09 mL, 9.08 mmol, 1.2 equiv.) in toluene (10 mL) was added trimethylaluminum (2M in hexanes, 5.6 mL, 11.4 mmol, 1.5 equiv.). The reaction mixture was stirred at 80° C. for 2 hours. The reaction mixture was concentrated. The resulting residue was dissolved in EtOAc (100 mL). The organic layer was washed with saturated NaHCO3, dried over Na2SO4, and concentrated. The resulting residue was purified on silica gel column using a mixture of hexanes and ethyl acetate to give N-(2-chlorobenzyl)-3-hydroxy-2,2-dimethylpropanamide (1.55 g, 84%). LRMS (M+H+) m/z 242.1. The reaction mixture was concentrated The resulting residue was dissolved in EtOAc (100 mL) The organic layer was washed with saturated NaHCO3 dried over Na2SO4 concentrated The resulting residue was purified on silica gel column a mixture of hexanes and ethyl acetate
Source ID: ord-74d8738b1782456c9ad0e5214729b31eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of N-(2-chlorobenzyl)-3-hydroxy-2,2-dimethylpropanamide (30 mg, 0.12 mmol), in CH2Cl2 were added DMAP and 4-ethylphenylisocyanate (21 μL, 0.15 mmol, 1.5 equiv.). The reaction mixture was stirred for 1 h. The reaction mixture was concentrated. The resulting residue was to purify on RP-HPLC to give 3-(2-chlorobenzylamino)-2,2-dimethyl-3-oxopropyl 4-ethylphenylcarbamate (10 mg, 17%). LRMS (M+H+) m/z 389.1. The reaction mixture was concentrated to purify on RP-HPLC
Source ID: ord-5902bfb0da7144359c909edba60c3015Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of N-(2-chlorobenzyl)-3-hydroxy-2,2-dimethylpropanamide (30 mg, 0.12 mmol), in CH2Cl2 were added DMAP and 4-ethylphenylisocyanate (21 μL, 0.15 mmol, 1.5 equiv.). The reaction mixture was stirred for 1 h. The reaction mixture was concentrated. The resulting residue was to purify on RP-HPLC to give 3-(2-chlorobenzylamino)-2,2-dimethyl-3-oxopropyl 4-ethylphenylcarbamate (10 mg, 17%). LRMS (M+H+) m/z 389.1. The reaction mixture was concentrated to purify on RP-HPLC
Source ID: ord-5902bfb0da7144359c909edba60c3015Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of methyl 3-hydroxy-2,2-dimethylpropanoate (1 g, 7.31 mmol) and 2-chlorobenzylamine (1 mL, 8.75 mmol, 1.2 equiv.) in toluene (7 mL) was added trimethylaluminum (2 M in hexane, 5.4 mL, 10.8 mmol, 1.5 equiv.). The reaction mixture was stirred at 80° C. for 2 h. The reaction mixture was quenched with saturated NaHCO3. The resulting mixture was extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated to give N-(2-chlorobenzyl)-3-hydroxy-2,2-dimethylpropanamide (1.5 g, 85%), which was used without further purification. LRMS (M+H+) m/z 242.1. The reaction mixture was quenched with saturated NaHCO3 The resulting mixture was extracted with EtOAc The organic layer was dried over Na2SO4 concentrated
Source ID: ord-afd96c4c71a64cd48db01043faa14c79Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-286eae15c5ea4000a3e3b94d9c9c85e6Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-4d01cab0424b4e2fa0d75a847ac32313Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of N-(2-chlorobenzyl)-3-hydroxy-2,2-dimethylpropanamide (0.50 g, 2.07 mmol) in THF (5 mL) were added phthalimide (0.457 g, 3.10 mmol, 1.5 equiv.) and PPh3 (0.813 g, 3.10 mmol, 1.5 equiv.). DIAD (600 μL, 3.10 mmol, 1.5 equiv.) was added dropwise into the reaction mixture. The resulting mixture was stirred overnight. LC/MS indicated that starting material was consumed. The reaction mixture was concentrated. The resulting residue was purified on silica gel column a mixture of hexanes and ethyl acetate to give N-(2-chlorobenzyl)-3-(1,3-dioxoisoindolin-2-yl)-2,2-dimethylpropanamide (0.50 g, 65%). LRMS (M+H+) m/z 371.1. was consumed The reaction mixture was concentrated The resulting residue was purified on silica gel column a mixture of hexanes and ethyl acetate
Source ID: ord-6acabc4af0fd41d781bd72884f793398Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of methyl 3-hydroxy-2,2-dimethylpropanoate (1.0 g, 7.57 mmol) and 2-chlorobenzylamine (1.09 mL, 9.08 mmol, 1.2 equiv.) in toluene (10 mL) was added trimethylaluminum (2M in hexanes, 5.6 mL, 11.4 mmol, 1.5 equiv.). The reaction mixture was stirred at 80° C. for 2 hours. The reaction mixture was concentrated. The resulting residue was dissolved in EtOAc (100 mL). The organic layer was washed with saturated NaHCO3, dried over Na2SO4, and concentrated. The resulting residue was purified on silica gel column using a mixture of hexanes and ethyl acetate to give N-(2-chlorobenzyl)-3-hydroxy-2,2-dimethylpropanamide (1.55 g, 84%). LRMS (M+H+) m/z 242.1. The reaction mixture was concentrated The resulting residue was dissolved in EtOAc (100 mL) The organic layer was washed with saturated NaHCO3 dried over Na2SO4 concentrated The resulting residue was purified on silica gel column a mixture of hexanes and ethyl acetate
Source ID: ord-74d8738b1782456c9ad0e5214729b31ePubChem References
These sources are listed in the compound's public database record.
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