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CAS No. : | 4070-48-8 | MDL No. : | MFCD03695472 |
Formula : | C6H13NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CEMZBWPSKYISTN-YFKPBYRVSA-N |
M.W : | 131.17 | Pubchem ID : | 94285 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P272-P280-P302+P352-P333+P313-P321-P363-P501 | UN#: | |
Hazard Statements: | H317 | Packing Group: | |
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 |
---|---|---|
77% | With thionyl chloride at 65℃; for 8h; | |
With thionyl chloride at 40℃; for 2h; | ||
With hydrogenchloride |
With thionyl chloride | ||
With acetyl chloride at 70℃; for 1h; | ||
With thionyl chloride at 0 - 20℃; | ||
With thionyl chloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tetrahydroborate; In tetrahydrofuran; | C. Synthesis of 2-amino-3-methyl-1-butanol Valine methyl ester (0.1 mol) is dissolved in dry THF, and NaBH4 (0.035 mol) is then added slowly. The reaction mixture is stirred at room temperature for about 4 hours, and the colorless solid is purified by the procedure described in part (A). | |
With sodium tetrahydroborate; In tetrahydrofuran; | C. Synthesis of 2-amino-3-methyl-1-butanol STR22 Valine methyl ester (0.1 mol) is dissolved in dry THF, and NaBH4 (0.035 mol) is then added slowly. The reaction mixture is stirred at room temperature for about 4 hours, and the colorless solid is purified by the procedure described in part (A). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; | |
88% | With 4-methyl-morpholine; (fluorenylmethoxy)carbonyl chloride In tetrahydrofuran at -15℃; for 0.583333h; | |
88% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1.08h; | General procedure for coupling reaction: General procedure: the methyl ester of the C-terminal amino acid (1 eq) and the Boc-protected N-terminal amino acid (1.1 eq) were dissolved in dry solvent CH2Cl2 (15 mL), followed by addition of DMAP (1 eq). The reaction mixture was stirred for 5 min at rt whereupon EDC (1.3 eq) was added. The reaction was there after stirred for 1 h at rt. The reaction mixture was then washed with H2O. The aqueous layer was extracted with AcOEt. The organic layer was dried on MgSO4, concentrated in vacuo and the crude product was purified by flash chromatography. |
84% | With phenylsilane In dichloromethane at 20℃; for 16h; | |
81% | Stage #1: <i>N</i>-<i>tert</i>-butoxycarbonyl-<i>L</i>-phenylalanine With triethylamine; N,N'-carbonyldisaccharin In dichloromethane at 20℃; for 3h; Stage #2: L-Valine methyl ester With triethylamine In dichloromethane at 20℃; for 13h; | |
51% | Stage #1: <i>N</i>-<i>tert</i>-butoxycarbonyl-<i>L</i>-phenylalanine With bis(2-chlorophenyl)borinic acid In fluorobenzene at 65℃; for 0.25h; Inert atmosphere; Molecular sieve; Stage #2: L-Valine methyl ester In fluorobenzene at 65℃; for 48h; Inert atmosphere; Molecular sieve; | |
50% | With (2-(thiophen-2-ylmethyl)phenyl)boronic acid In fluorobenzene at 65℃; for 24h; Inert atmosphere; Molecular sieve; | |
(i) ClCO2Et, Et3N, (ii) /BRN= 1721775/; Multistep reaction; | ||
With 3-(5-nitro-2-oxo-1,2-dihydro-1-pyridyl)-1,2-benzisothiazole 1,1,-dioxide; triethylamine 1) dichloromethane, -10 deg C -> 0 deg C, 2 h; 2) dichloromethane, 0 deg C, 2 h, r.t., overnight; Yield given. Multistep reaction; | ||
With N,N'-carbonyldi<2(3H)-benzoxazolethione; TEA 1) dichloromethane, 0 deg C, 3 h, 2) r.t., 12 h; Yield given. Multistep reaction; | ||
With TEA; 3-(5-nitro-2-oxo-1,2-dihydro-1-pyridyl)-1,2-benzisothiazole 1,1,-dioxide 1) dichloromethane, -10 deg C, 2 h, 2) 0 deg C, 2 h; Yield given. Multistep reaction; | ||
With triethylamine; isobutyl chloroformate | ||
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 12h; | ||
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; Cooling with ice; | ||
With triethylamine; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; | ||
With benzotriazol-1-ol; dicyclohexyl-carbodiimide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With cyclohexene In ethanol Heating; | ||
With hydrogen In methanol for 5h; Ambient temperature; | ||
Multi-step reaction with 4 steps 1: 65 percent / p-TsOH / toluene / 100 °C 2: NaHCO3 / methanol; H2O / Heating 3: H2 / Pd/C / methanol / 12 h / 20 °C 4: HCl / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With dicyclohexyl-carbodiimide In tetrahydrofuran for 2h; Ambient temperature; | |
50% | With dicyclohexyl-carbodiimide In tetrahydrofuran for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With pentafluorophenyl diphenyl-phosphinate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 2h; Ambient temperature; | |
85% | With N,N'-bis-(1H,1H,2H,2H-perfluorooctyl)carbodiimide In dichloromethane at 20℃; for 16h; | |
83% | With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0℃; for 72h; |
71% | With tributylphosphine; diphenyl diselenide; benzalacetophenone In dichloromethane; N,N-dimethyl-formamide Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With dicyclohexyl-carbodiimide In chloroform at -5℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -15℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In benzene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With zinc In tetrahydrofuran for 0.25h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium 4-tert-butylphenolate; sodium t-butanolate In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In dichloromethane at 0 - 20℃; | |
90% | With triethylamine In tetrahydrofuran at 20℃; for 24h; | |
90% | With triethylamine In tetrahydrofuran for 8h; |
87% | With fipronilβ-cyclodextrin In methanol; acetone at 20℃; for 0.166667h; | |
With triethylamine In tetrahydrofuran at 20 - 50℃; | ||
With triethylamine In dichloromethane | ||
137.2 mg | at 20℃; Ionic liquid; | |
With sodium hydrogencarbonate In ethanol at 0 - 20℃; | ||
With triethylamine In dichloromethane at 0 - 25℃; | B Step B (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate (19b) Step B (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate (19b)To a solution of the crude 19a (11.19 g, 0.00854 mol) in CH2Cl2 (200 mL) at 0°C was added triethylamine (61.8 mL, 0.427 mol) and Di-tert-butyl dicarbonate (Boc2O, 27.8 g, 0.128 mol). The reaction mixture was warmed to room temperature and stirred overnight. To the reaction mixture was added dichloromethane. The organic layer washed with water and brine, dried over anhydrous Na2SO4 and concentrated to dryness. The residue was purified by column chromatography over silica gel using 10% ethyl acetate in hexane (v/v) to yield 19b (15.5 g). 1H NMR (400 MHZ, DMSO-d6) : δ 7.18 (d, J=8.00 Hz, 1H), 3.83 (t, J=6.80 Hz, 1H), 3.68 (s, 3H), 2.03- 1.94 (m, 1H), 1.47 (s, 9H), 0.91-0.86 (m, 6H). | |
In tetrahydrofuran; methanol at 0 - 20℃; for 18h; | ||
102 mg | With sodium hydroxide In water; acetonitrile for 0.5h; Inert atmosphere; | |
With triethylamine In dichloromethane at 0 - 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With phosphoric acid In tetrahydrofuran at 20℃; | |
97% | With phosphoric acid In dichloromethane at 20℃; for 3h; | |
Stage #1: N-tert-butoxycarbonyl-L-valine methyl ester With trifluoroacetic acid In dichloromethane at 20℃; for 0.5h; Stage #2: With sodium hydroxide In dichloromethane; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate In water | ||
With sodium hydrogencarbonate at 20℃; | ||
With triethylamine In dichloromethane at 0 - 20℃; for 11h; | 28.2 Step 2 Step 2. To the solution of 28-2 (2.6 g, 5 mmol) in DCM (50 mL) was added TEA (2 mL) and stirred at 0 °C until the solution became clear. CbzCl (10.2 g, 6 mmol) was then added dropwise in 1 h and maintain the temperature below 5 °C. The mixture was then stirred at r.t. for another 10 h. Solution was taken up with DCM (100 mL) and washed with aq. HC1, aq. NaHC03 and water, organic layer was dried over anhydrous Na2S04, and solvents were then evaporated to give 28-3. LCMS (ESI): m/z 265.9 [M+H+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | Stage #1: (3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid With benzotriazol-1-ol In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: L-Valine methyl ester With 4-methyl-morpholine; dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 18h; | |
95% | With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 2.462 g / Et3N / CH2Cl2 2: H2O; Acylase I on Eupergit C / 27 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N,N-dicyclohexylcarbodiimide / CH2Cl2 2: HCl / CH2Cl2 / 0 °C 3: 1.) aq. sodium bicarbonate / 1.) room temperature; 2.) reflux, methanol, 24 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 82 percent / CH2Cl2 / 72 h / Ambient temperature 2: 1) n-LiBu / 1) THF, hexane, -70 deg C, 10 min; 2) -70 deg C, THF, 5 h 3: 0.25 N HCl / 10 h / Ambient temperature | ||
Multi-step reaction with 3 steps 1: 82 percent / CH2Cl2 / 72 h / Ambient temperature 2: 1) n-LiBu / 1) THF, hexane, -70 deg C, 10 min; 2) -70 deg C, THF, 5 h 3: 0.25 N HCl / 10 h / Ambient temperature | ||
Multi-step reaction with 3 steps 1: 82 percent / CH2Cl2 / 72 h / Ambient temperature 2: 1) n-LiBu / 1) THF, hexane, -70 deg C, 10 min; 2) -70 deg C, THF, 5 h 3: 0.25 N HCl / 10 h / Ambient temperature |
Multi-step reaction with 3 steps 1: 82 percent / CH2Cl2 / 72 h / Ambient temperature 2: 1) n-LiBu / 1) THF, hexane, -70 deg C, 10 min; 2) -70 deg C, THF, 5 h 3: 1) 0.25 N HCl; 2) conc. HCl / 1) 10 h, room temp. | ||
Multi-step reaction with 3 steps 1: 82 percent / CH2Cl2 / 72 h / Ambient temperature 2: 1) n-LiBu / 1) THF, hexane, -70 deg C, 10 min; 2) -70 deg C, THF, 5 h 3: 0.25 N HCl / 10 h / Ambient temperature | ||
Multi-step reaction with 3 steps 1: 82 percent / CH2Cl2 / 72 h / Ambient temperature 2: 1) n-LiBu / 1) THF, hexane, -70 deg C, 10 min; 2) -70 deg C, THF, 5 h 3: 0.25 N HCl / 10 h / Ambient temperature | ||
Multi-step reaction with 3 steps 1: 82 percent / CH2Cl2 / 72 h / Ambient temperature 2: 1) n-LiBu / 1) THF, hexane, -70 deg C, 10 min; 2) -70 deg C, THF, 5 h 3: 0.25 N HCl / 10 h / Ambient temperature | ||
Multi-step reaction with 4 steps 2: 1) BuLi / 1) THF, -78deg C; 2) THF 4: 0.25N aq. / Ambient temperature | ||
Multi-step reaction with 3 steps 2: 1) BuLi / 1) THF, -78 deg C; 2) THF 3: aq. HCl / Ambient temperature | ||
Multi-step reaction with 3 steps 2: 1) n-BuLi / 1) THF, -78 deg C; 2) THF 3: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 3 steps 2: 1) BuLi / 1) THF, -78 deg C; 2) THF 3: aq. HCl / Ambient temperature | ||
Multi-step reaction with 3 steps 2: 1) n-BuLi / 1) THF, -78 deg C; 2) THF 3: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 3 steps 2: 1) n-BuLi / 1) THF, -78 deg C; 2) THF 3: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 3 steps 2: 1) n-BuLi / 1) THF, -78 deg C; 2) THF 3: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 3 steps 2: 1) n-BuLi / 1) THF, -78 deg C; 2) THF 3: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 3 steps 2: 1) n-BuLi / 1) THF, -78 deg C; 2) THF 3: 0.25N aq. HCl / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 2: Heating 4: 1) BuLi / 1) THF, -70 deg C; 2) THF 5: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 6 steps 2: Heating 4: 1) BuLi / 1) THF, -70 deg C; 2) THF 5: thionyl chloride / pyridine 6: aq. HCl | ||
Multi-step reaction with 6 steps 2: Heating 4: 1) BuLi / 1) THF, -70 deg C; 2) THF 5: thionyl chloride / pyridine 6: aq. HCl |
Multi-step reaction with 5 steps 2: Heating 4: 1) BuLi / 1) THF, -70 deg C; 2) THF 5: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 5 steps 2: Heating 4: 1) BuLi / 1) THF, -70 deg C; 2) THF 5: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 5 steps 2: Heating 4: 1) BuLi / 1) THF, -70 deg C; 2) THF 5: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 5 steps 2: Heating 4: 1) BuLi / 1) THF, -70 deg C; 2) THF 5: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 5 steps 2: Heating 4: 1) BuLi / 1) THF, -70 deg C; 2) THF 5: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 5 steps 2: Heating 4: 1) BuLi / 1) THF, -70 deg C; 2) THF 5: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 5 steps 2: Heating 4: 1) BuLi / 1) THF, -70 deg C; 2) THF 5: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 5 steps 2: Heating 4: 1) BuLi / 1) THF, -70 deg C; 2) THF 5: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 5 steps 2: Heating 4: 1) BuLi / 1) THF, -70 deg C; 2) THF 5: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 6 steps 2: Heating 4: 1) BuLi / 1) THF, -78deg C; 2) THF 6: 0.25N aq. / Ambient temperature | ||
Multi-step reaction with 5 steps 2: Heating 4: 1) BuLi / 1) THF, -78 deg C; 2) THF 5: aq. HCl / Ambient temperature | ||
Multi-step reaction with 5 steps 2: Heating 4: 1) n-BuLi / 1) THF, -78 deg C; 2) THF 5: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 5 steps 2: Heating 4: 1) BuLi / 1) THF, -78 deg C; 2) THF 5: aq. HCl / Ambient temperature | ||
Multi-step reaction with 5 steps 2: Heating 4: 1) n-BuLi / 1) THF, -78 deg C; 2) THF 5: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 5 steps 2: Heating 4: 1) n-BuLi / 1) THF, -78 deg C; 2) THF 5: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 5 steps 2: Heating 4: 1) n-BuLi / 1) THF, -78 deg C; 2) THF 5: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 5 steps 2: Heating 4: 1) n-BuLi / 1) THF, -78 deg C; 2) THF 5: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 5 steps 2: Heating 4: 1) n-BuLi / 1) THF, -78 deg C; 2) THF 5: 0.25N aq. HCl / Ambient temperature | ||
Multi-step reaction with 5 steps 1: triethylamine / tetrahydrofuran; CHCl3 / 1.) 3 h, - 70 degC, 2.) 30 min, room temp. 2: toluene / 12 h / Heating 3: 89 percent / CH2Cl2 / 72 h 4: 1.) n-C4H9Li / 1.) THF, hexane, 15 min, -70 degC, 2.) 10 h, -70 degC 5: 1.) aq. HCl, 2.) aq. NH3 / diethyl ether / 72 h / Ambient temperature | ||
Multi-step reaction with 5 steps 1: triethylamine / tetrahydrofuran; CHCl3 / 1.) 3 h, - 70 degC, 2.) 30 min, room temp. 2: toluene / 12 h / Heating 3: 89 percent / CH2Cl2 / 72 h 4: 1.) n-C4H9Li / 1.) THF, hexane, 15 min, -70 degC, 2.) 24 h, -70 degC 5: 1.) aq. HCl, 2.) aq. NH3 / diethyl ether / 192 h / Ambient temperature | ||
Multi-step reaction with 5 steps 1: triethylamine / tetrahydrofuran; CHCl3 / 1.) 3 h, - 70 degC, 2.) 30 min, room temp. 2: toluene / 12 h / Heating 3: 89 percent / CH2Cl2 / 72 h 4: 1.) n-C4H9Li / 1.) THF, hexane, 15 min, -70 degC, 2.) 12 h, -70 degC 5: 1.) aq. HCl, 2.) aq. NH3 / diethyl ether / 72 h / Ambient temperature | ||
Multi-step reaction with 5 steps 1: triethylamine / tetrahydrofuran; CHCl3 / 1.) 3 h, - 70 degC, 2.) 30 min, room temp. 2: toluene / 12 h / Heating 3: 89 percent / CH2Cl2 / 72 h 4: 1.) n-C4H9Li / 1.) THF, hexane, 15 min, -70 degC, 2.) 12 h, -70 degC 5: 1.) aq. HCl, 2.) aq. NH3 / diethyl ether / 72 h / Ambient temperature | ||
Multi-step reaction with 5 steps 1: triethylamine / tetrahydrofuran; CHCl3 / 1.) 3 h, - 70 degC, 2.) 30 min, room temp. 2: toluene / 12 h / Heating 3: 89 percent / CH2Cl2 / 72 h 4: 1.) n-C4H9Li / 1.) THF, hexane, 15 min, -70 degC, 2.) 12 h, -70 degC 5: 1.) aq. HCl, 2.) aq. NH3 / diethyl ether / 72 h / Ambient temperature | ||
Multi-step reaction with 5 steps 1: triethylamine / tetrahydrofuran; CHCl3 / 1.) 3 h, - 70 degC, 2.) 30 min, room temp. 2: toluene / 12 h / Heating 3: 89 percent / CH2Cl2 / 72 h 4: 1.) n-C4H9Li / 1.) THF, hexane, 15 min, -70 degC, 2.) 8 h, -70 degC 5: 1.) aq. HCl, 2.) aq. NH3 / diethyl ether / 72 h / Ambient temperature | ||
Multi-step reaction with 5 steps 1: triethylamine / tetrahydrofuran; CHCl3 / 1.) 3 h, - 70 degC, 2.) 30 min, room temp. 2: toluene / 12 h / Heating 3: 89 percent / CH2Cl2 / 72 h 4: 1.) n-C4H9Li / 1.) THF, hexane, 15 min, -70 degC, 2.) 8 h, -70 degC 5: 1.) aq. HCl, 2.) aq. NH3 / diethyl ether / 72 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | Stage #1: 1-(tert-butoxycarbonyl)-L-proline With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -15℃; for 0.166667h; Stage #2: L-Valine methyl ester In tetrahydrofuran at -15 - 20℃; | General procedure: To a stirred solution of N-Boc-l-proline 1.07 g (5.0 mmol) and THF 40 mL, at -15 °C, were slowly added 0.65 mL of NMM (5.5 mmol) and 0.67 mL of isobutyl chlorofomate (5.0 mmol). After the solution was stirred for 10 min, l-valine methyl ester 0.92 g (5.5 mmol), which was dissolved in NMM 0.65 mL (5.5 mmol) and 60 mL THF, was added to the reaction mixture. After 30 min, the reaction mixture was allowed to warm to room temperature and stirred overnight. The solution was concentrated under reduced pressure and the residue was re-dissolved in ethyl acetate (50 mL). The solution was washed with saturated NaHCO3 solution, brine, 1 N citric acid solution, and water (50 mL each). The organic layer was dried over anhydrous Na2SO4 and concentrated to give a white solid 1.61 g (4.9 mmol, 98%). This white solid was dissolved in 30 mL methanol and cooled to 0 °C followed by the addition of 2 N KOH solution 15 mL. The reaction mixture was allowed to warm to room temperature and stirred for 4 h. The methanol was removed under reduced pressure, the residue was cooled to 0 °C, and HCl 60 mL (5%) was added to the mixture. The aqueous layer was extracted with ethyl acetate (3×60 mL). The combined organic layer was dried over anhydrous Na2SO4 and concentrated to yield Boc-Pro-Val-OH as a white solid 1.32 g (4.2 mmol, 85%). |
97% | Stage #1: 1-(tert-butoxycarbonyl)-L-proline; L-Valine methyl ester With benzotriazol-1-ol In tetrahydrofuran at 0℃; for 0.333333h; Inert atmosphere; Stage #2: With triethylamine In tetrahydrofuran Inert atmosphere; Stage #3: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran Inert atmosphere; | |
95% | With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane Inert atmosphere; |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | ||
Stage #1: 1-(tert-butoxycarbonyl)-L-proline With benzotriazol-1-ol; dicyclohexyl-carbodiimide In chloroform at 0℃; for 0.5h; Stage #2: L-Valine methyl ester In chloroform at 0 - 20℃; for 10h; | ||
Stage #1: 1-(tert-butoxycarbonyl)-L-proline With N-ethyl-N,N-diisopropylamine; isobutyl chloroformate Stage #2: L-Valine methyl ester With N-ethyl-N,N-diisopropylamine | ||
With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 55℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 21h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In dichloromethane at 20℃; for 4h; | |
100% | With sodium hydrogencarbonate In dichloromethane; water at 25℃; for 4h; | |
104.6 mg | In dichloromethane; water at 20℃; for 4h; Alkaline conditions; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 12h; | General procedure: The fatty acid (0.8 mmol), dicyclohexyl carbodiimide (0.8 mmol), and (dimethylamino)pyridine (0.088 mmol) was added to a flask with 10 mL CH2Cl2. The mixture was stirred for 5 min. In a second flask the amino ester (1.76 mmol) was dissolved in 10 mL of CH2Cl2 and Et3N (2.64 mmol); the mixture was stirred for 10 min at room temperature. The solution of amino ester was slowly added to the mixture of fatty acid and stirred for 12 h at room temperature. After the reaction, white precipitate (dicyclohexylurea) was separated by filtration. The product was purified by column chromatography on silica gel using hexane:ethyl acetate (7:3) as the eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: dicyclohexyl-carbodiimide / tetrahydrofuran / 0.08 h / 0 - 5 °C 1.2: 40 h 2.1: hydrogenchloride / methanol / 5 h 3.1: sodium hydroxide / water 3.2: pH Ca. 6 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With sulfated tungstate In toluene for 18h; Reflux; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | General procedure: To a solution of <strong>[227626-60-0]2-(1-(((tert-butoxycarbonyl)amino)methyl)cyclohexyl)acetic acid</strong> 16c (0.50 g, 1.84 mmol) in dry THF (30 mL)N-methylmorpholine was added (0.20 mL, 1.84 mmol) and the mixture was stirred at rt for 10min under nitrogen. After cooling to 0 C,isobutyl chloroformate (0.18 mL, 1.84mmol) was added dropwise.N-Methylmorpholine (0.20 mL, 1.84 mmol) was then added in 4 min followed by the addition of nucleophile (1.84 mmol) then stirred for 24 h at rt under nitrogen. After the solvent was evaporated, ethyl acetate (30 mL) was added to the crude and solution was washed with 2 N HCl solution (2 x 50 mL) and saturated sodium carbonate solution (2 30 mL). The organic phasewas dried over anhyd magnesium sulfate and solvent was removed to give the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 45% 2: 39% | With palladium diacetate; triethylamine; triphenylphosphine at 50℃; for 94h; Inert atmosphere; | 5.13 4.2 Aminocarbonylation of 7-iodoindole in the presence of various amines as N-nucleophiles under atmospheric carbon monoxide pressure General procedure: In a typical experiment Pd(OAc)2 (5.6mg, 0.025mmol), triphenylphosphine (13.1mg, 0.05mmol), 7-iodoindole (243mg, 1mmol) or 5-bromo-7-iodoindole (322mg, 1mmol), amine nucleophile (3mmol of a/2mmol of b/1.5mmol of c, d/1.1mmol of e, f, g, h) and triethylamine (0.5mL) were dissolved in DMF (10mL) under argon in a three-necked flask equipped with a gas inlet, reflux condenser with a ballon (filled with argon) at the top. The atmosphere was changed to carbon monoxide. The reaction was conducted for the given reaction time upon stirring at 50°C and analysed by GC-MS (internal standard: naphthalene). The mixture was then concentrated and evaporated to dryness. The residue was dissolved in chloroform (20mL) and washed with water (3×20mL). The organic phase was dried over Na2SO4, filtered and evaporated to a crystalline material or a waxy residue. All compounds were subjected to column chromatography (Silicagel 60 (Merck), 0.063-0.200mm), EtOAc/CHCl3, or EtOAc/toluene, or hexane/EtOAc/MeOH (the exact ratios are specified in Section Characterization (3.4) for each compound). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With benzotriazol-1-ol; dicyclohexyl-carbodiimide In acetonitrile at 0 - 23℃; for 18h; | General procedure for the synthesis of methyl 2-(4-(phthalimido-2-yl)butanamido)alkyl carboxylates (14-23) General procedure: To acold solution of the amino acid ester (1.50 mmol), at - 5 °C,in MeCN (15 mL), 4-(phthalimido-2-yl)butyric acid (2)(350 mg, 1.50 mmol), HOBt (203 mg, 1.50 mmol) andN,N′-dicyclohexylcarbodiimide (DCC) (309 mg, 1.5 mmol)were added successively. The reaction mixture was stirredat 0 °C for 1 h, at 5 °C for 1 h, and at 23 °C for 16 h.Dicyclohexylurea (DCU) was filtered, and the filtrate wasevaporated to dryness and the residue was dissolved in ethylacetate, filtered, washed successively with saturated NaClsolution, 5% NaHCO3 solution, 1M HCl, followed bywashing with saturated NaCl solution and finally withwater. The residue was dried (Na2SO4), filtered, evaporatedto dryness and purified on a SiO2 column (10 g). Elutionwith MeOH (0-10) and CHCl3 as an eluent afforded thepure amide derivative. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In chloroform; at 60℃; for 8h; | General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), EDCHCl (42.2 mg, 0.22 mmol), HOBt (29.7 mg,0.22 mmol), Et3N (102 L, 0.30 mmol) and various amino acid esters (0.30 mmol) in CHCl3 (10 mL)was stirred at 60 C for 8 h. After confirming the reaction progress by thin-layer chromatography, thesolvent was evaporated in vacuo, the mixture was dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then purified using silica gel column chromatography andeluted with a gradient of petroleum ether:ethyl acetate (10:1-5:1) to obtain the target compound3a-3d. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In aq. buffer; at 37℃;pH 7.3; | General procedure: <strong>[1236199-60-2]NL-101</strong> (0.03 g) was incubated with amino acids (0.02 g) and peptides (0.03 g) at 37 oC in a buffer solution, which pH was 5.3,7.3 and 9.3 respectively as the experimental surroundings. The pH of the samples was determined by a pH-meter (FE 20, MettlerToledo). All samples were kept at -20 oC until further analysis. The desalting step of the <strong>[1236199-60-2]NL-101</strong> adducts obtained under theexperimental conditions was not carried out before MS analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: 5-tert-butyl N-benzyloxycarbonyl-L-glutamate With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; for 0.5h; Inert atmosphere; Stage #2: L-Valine methyl ester With 4-methyl-morpholine In tetrahydrofuran at -20 - 20℃; for 19h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With oxygen; 3,6-di(2'-pyridyl)-1,2,4,5-tetrazine In tetrahydrofuran at 20℃; for 5h; | General experimental procedure for the synthesis of amide General procedure: Thioacids (1 mmol, 1.0 equiv.), pytz (0.1 mmol, 0.1 equiv.) in THF (5 mL) were placed in a 50 mL round bottom flask and amines (1 mmol, 1.0 equiv.) dissolved in 5 mL THF was then added to it slowly under oxygen. The reaction mixture was stirred at room temperature for 4-7 h. When the reaction was completed (monitored by TLC), reaction mixture was evaporate to dryness at room temperature under vacuum. The residue was re-dissolved in chloroform (5 mL), washed with water and brine and dried over anhydrous Na2SO4. After filtration and removal of solvent, the residue was purified by flash column chromatography (hexane/ethyl acetate, 10:1) to afford the desired products 3aa-3as, 3ba-3bc, 3bt. |
Tags: 4070-48-8 synthesis path| 4070-48-8 SDS| 4070-48-8 COA| 4070-48-8 purity| 4070-48-8 application| 4070-48-8 NMR| 4070-48-8 COA| 4070-48-8 structure
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