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CAS No. : | 89711-08-0 | MDL No. : | MFCD01321273 |
Formula : | C7H13NO3 | Boiling Point : | - |
Linear Structure Formula : | (CH3)3COCONHCH2CHO | InChI Key : | ACNRTYKOPZDRCO-UHFFFAOYSA-N |
M.W : | 159.18 | Pubchem ID : | 4247255 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Methyl 3-((2-((tert-butoxycarbonyl)amino)ethyl)amino)-4-fluorobenzoate (I-44)Methyl 3-amino-4-fluorobenzoate (8.4 mmol) and tert-butyl (2-oxoethyl)carbamate (12.6 mmol) were dissolved in MeOH (100 ml_) and AcOH (10 ml_). After stirring for 1 hr at room temperature the reaction mixture was treated with NaCNBH3(16.6 mmol) and stirred for 2 hrs. After removal of solvent (aspirator) the mixture was dissolved in EtOAc and washed with NaHC03(sat., 1x). The aqueous phase was washed with EtOAc (1x) and the combined organic layers were dried (MgSO^. The product (I-44) was taken on crude for the next step. 1H NMR (400 MHz, CDCl3): delta 7.40-7.38 (m, 2H), 7.02 (dd, J = 8.8 Hz, 11 .1 , 1 H), 4.88 (s, 1 H), 3.91 (s, 3H), 3.40-3.38 (m, 4H), 1.47 (s, 9H). MS (m/z): 313.1 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Potassium hydroxide (73.9 mg, 1.3 177 mmol%) and tert-butyl N-[(2R)-2-bromopropyl]carbamate (230.1mg, 0.96634 mmol) are added to a solution of <strong>[89830-98-8]4-cyclopropyl-1H-imidazole</strong> (100 mg, 0.087849 mmol) in DMSO (2 mL) at 0 C. The mixture is stirred at room temperature for 65 hours. The reaction is quenched with water and extracted with EtOAc (3x). The organic extracts are washed with saturated NaC1 (3x), dried over Na2SO4, filtered, and concentrated to dryness. The residue is purified bysilica gel flash chromatography with 4% MeOH in DCM to give the title compounds as a mixture of 2 regioisomers (112 mg, 22.82%) and as a yellow oil. ES/MS (m/z): 266 (M+ 1). TFA (2 mL, 26.45 mmol) is added to racemic tert-butyl N-[2-(4-cyclopropylimidazol- i-yl)-i -methyl-ethyl] carbamate and to racemic tert-butyl N- [2-(5 -cyclopropylimidazol-1-yl)-1-methyl-ethyl]carbamate (112 mg, 0.2005 mmol) in DCM(10 mL) at room temperature. The mixture is stirred at room temperature for 1 hour andis concentrated to give the crude title compounds as a mixture of regioisomers (69.8 mg,100%) as a yellow oil. ES/MS (m/z): 166 (M+1). Sodium triacetoxyborohydride (56.9 mg, 0.260 mmol) is added to a solution of racemi c-i -(4-cyclopropylimidazol -1 -yl)propan-2-amine and racemic- 1 -(5- cyclopropylimidazol- 1 -yl)propan-2-amine (69.7 mg, 0.200 mmol) and tert-butyl N-(2- oxoethyl)carbamate (33.6 mg, 0.200 mmol) in DCM (5 mL) and acetic acid (15.6 mg, 0.260 mmol) at room temperature. The mixture is stirred at room temperature for 18 hours. The reaction is quenched by the addition of saturated NaHCO3. The mixture is extracted with DCM (3x), the organic extracts are dried over Na2SO4, filtered, and concentrated to give the crude title compound as a mixture of regioisomers (130 mg, 100%) as a yellow oil. ES/MS (m/z): 309 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Potassium hydroxide (73.9 mg, 1.3 177 mmol%) and tert-butyl N-[(2R)-2-bromopropyl]carbamate (230.1mg, 0.96634 mmol) are added to a solution of <strong>[89830-98-8]4-cyclopropyl-1H-imidazole</strong> (100 mg, 0.087849 mmol) in DMSO (2 mL) at 0 C. The mixture is stirred at room temperature for 65 hours. The reaction is quenched with water and extracted with EtOAc (3x). The organic extracts are washed with saturated NaC1 (3x), dried over Na2SO4, filtered, and concentrated to dryness. The residue is purified bysilica gel flash chromatography with 4% MeOH in DCM to give the title compounds as a mixture of 2 regioisomers (112 mg, 22.82%) and as a yellow oil. ES/MS (m/z): 266 (M+ 1). TFA (2 mL, 26.45 mmol) is added to racemic tert-butyl N-[2-(4-cyclopropylimidazol- i-yl)-i -methyl-ethyl] carbamate and to racemic tert-butyl N- [2-(5 -cyclopropylimidazol-1-yl)-1-methyl-ethyl]carbamate (112 mg, 0.2005 mmol) in DCM(10 mL) at room temperature. The mixture is stirred at room temperature for 1 hour andis concentrated to give the crude title compounds as a mixture of regioisomers (69.8 mg,100%) as a yellow oil. ES/MS (m/z): 166 (M+1). Sodium triacetoxyborohydride (56.9 mg, 0.260 mmol) is added to a solution of racemi c-i -(4-cyclopropylimidazol -1 -yl)propan-2-amine and racemic- 1 -(5- cyclopropylimidazol- 1 -yl)propan-2-amine (69.7 mg, 0.200 mmol) and tert-butyl N-(2- oxoethyl)carbamate (33.6 mg, 0.200 mmol) in DCM (5 mL) and acetic acid (15.6 mg, 0.260 mmol) at room temperature. The mixture is stirred at room temperature for 18 hours. The reaction is quenched by the addition of saturated NaHCO3. The mixture is extracted with DCM (3x), the organic extracts are dried over Na2SO4, filtered, and concentrated to give the crude title compound as a mixture of regioisomers (130 mg, 100%) as a yellow oil. ES/MS (m/z): 309 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | Acetic acid (42 pL, 0.73 mmcl) was added to a solution of 1 -(tert-butyl) 2-methyl (2S,4R)-4-aminopyrrolidine- 1 ,2-dicarboxylate (7.48 g, 30.6 mmcl) and tert-butyl (2-oxoethyl)carbamate (4.64 g, 29.2 mmcl) in MeOH (194 mL) and the reaction stirred at roomtemperature for 3 h. The solution was cooled to 0 00 and sodium triacetoxyborohydride (9.27 g,43.7 mmol) was added portion-wise. The reaction stirred overnight while slowly warming toroom temperature. The reaction mixture was concentrated under reduced pressure and theresulting residue was diluted with DCM washed sequentially with saturated sodiumbicarbonate, water and saturated sodium chloride. The organic layer was dried over Na2SO4, filtered and concentrated to dryness. The crude material was purified by silica gel chromatography (DCM/EtOAc/MeOH) to afford 1 -tert-butyl 2-methyl (2S,4R)-4-[2-(tert- butoxycarbonylamino)ethylamino]pyrrolidine- 1 ,2-dicarboxylate (Intermediate 72, 4.77 g, 42%yield) as a colorless oil. 1H NMR (500MHz, DMSO-d6) 51.25- 1.48 (20H, m), 1.84-2.07 (3H,m), 2.88-2.98 (2H, m), 3.02-3.17 (1H, m), 3.17-3.27 (1H, m), 3.40-3.51 (1H, m), 3.64(3H,s), 4.14-4.24 (1 H, m), 6.63-6.74 (1 H, m); m/z: (ESj [M+H] = 388. |