Alternatived Products of [ 1011479-75-6 ]
Product Details of [ 1011479-75-6 ]
| CAS No. : | 1011479-75-6 |
MDL No. : | MFCD20126212 |
| Formula : |
C14H23NO6
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | FYUPJGXEWFMXHW-UHFFFAOYSA-N |
| M.W : |
301.34
|
Pubchem ID : | 57415897 |
| Synonyms : |
|
Safety of [ 1011479-75-6 ]
Application In Synthesis of [ 1011479-75-6 ]
* 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.
- Downstream synthetic route of [ 1011479-75-6 ]
- 1
-
azetidine-3,3-dicarboxylic acid diethyl ester
[ No CAS ]
-
[ 24424-99-5 ]
-
[ 1011479-75-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 15h; |
1
To the crude Azetidine-3,3-dicarboxylic acid diethyl ester (1.38 g, 6.86 mmol) dissolved in THF (23 ml) is added BOC2O (1.65 g, 7.54 mmol), DIPEA (3 ml, 21 mmol) and a catalytic amount of DMAP (82.8 mg, 0.68 mmol). The mixture is stirred for 15 hours at room temperature. Water (100 ml) is added and the organic phase is separated. The aqueous layer is extracted with EtOAc (3x). The combined organic layers are dried over sodium sulfate, filtered and evaporated. |
|
With sodium carbonate In dichloromethane at 20℃; for 0.5h; |
11.a
1-Benzyl-azetidine-3,3-dicarboxylic acid diethyl ester (1.9 g; 0.05 mmol) (Synth. Commun. 2003, 33(19), 3347), ammonium formate (2.0 g) and Pd/C (10%, 200 mg) in EtOH are re- fluxed for 50 minutes, filtered, evaporated, taken up in CH2CI2 and extracted with water/10% acetic acid. The aqueous phase is adjusted to pH 10 by adding 2N Na2CO3 , combined with (BoC)2O (2.8 g) in CH2CI2, and stirred for 30 minutes at room temperature. The organic phase is dried over Na2SO4, evaporated to dryness and purified via chromatography (SiO2; TBME/hexanes 5:95 > 15:85) to yield the title compound as colorless oil. 1 H-NMR (400MHz; DMSO-d6: 4.17 (q, 4H); 3.33 (bs, 4H); 1.39 (s, 9H); 1.21 (t, 6H). MS (m/z) ES+: 302 (30, MH+); 202 (100). |
- 2
-
[ 1011479-75-6 ]
-
[ 1011479-76-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: 1-(tert-butyl) 3,3-diethyl azetidine-1,3,3-tricarboxylate With sodium hydroxide; ethanol; water for 39h;
Stage #2: With hydrogenchloride; water In ethanol |
1
Crude Azetidine-1 , 3, 3-tricarboxylic acid 1-tert-butyl ester 3,3-diethyl ester (1.57 g, 3.12 mmol) is dissolved in EtOH (21 ml) and treated with 1 N-NaOH solution. After stirring for 39 hours the mixture is diluted with water (20 ml) and the pH is adjusted to 1 by adding 0.5 N- HCI solution. After extraction with EtOAc (3x100 ml), the organic layer is dried over sodium sulfate and concentrated. |
|
Stage #1: 1-(tert-butyl) 3,3-diethyl azetidine-1,3,3-tricarboxylate With sodium hydroxide; water In ethanol at 5 - 50℃; for 1.08333h;
Stage #2: With hydrogenchloride In ethanol; water |
11.b
Azetidine-1 ,3,3-tricarboxylic acid 1-tert-butyl ester 3,3-diethyl ester (1.2 g; 0.4 mmol) in EtOH (12 ml) is cooled to 5 0C under stirring and combined with NaOH (60 mg; 0.04 mmol) in water (4 ml). The reaction mixture is left at room temperature for 1 hour, heated to 50 0C for 5 minutes, poured on brine, acidified with 2N HCI and extracted with TBME three times. The reaction mixture is extracted with TBME three times, the organic phases are combined, dried over Na2SO4 and evaporated to dryness, yielding the desired product as colorless crystals. 1 H-NMR (400MHz; DMSO-d6: 13.58 (bs, 1 H); 4.20 (q, 2H); 4.12 (bs, 4H); 1.39 (s, 9H); 1.21 (t, 3H). MS (m/z) ES+: 274 (30; MH+); 174 (100). |
- 3
-
[ 1011479-75-6 ]
-
C49H50Cl2F3N5O14
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 h / 0 - 20 °C
5: triethylamine; dmap / dichloromethane / 18 h / 0 - 20 °C |
|
- 4
-
[ 1011479-75-6 ]
-
C49H51ClF3N5O14
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 h / 0 - 20 °C
5: triethylamine; dmap / 16 h / 0 - 20 °C |
|
- 5
-
[ 1011479-75-6 ]
-
C37H43ClN4O11
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 h / 0 - 20 °C |
|
- 6
-
[ 1011479-75-6 ]
-
C43H44Cl2F3N5O12
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 6 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 h / 0 - 20 °C
5: triethylamine; dmap / dichloromethane / 18 h / 0 - 20 °C
6: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane; ethyl acetate / 1 h / 20 °C / Inert atmosphere |
|
- 7
-
[ 1011479-75-6 ]
-
diethyl 1-[(6S,14R,16S,24S)-14-[(3-chlorobenzoyl)amino]-9-[4-chloro-3-(trifluoromethyl)phenyl]-2,8,11-trioxo-7,18-dioxa-3,9,12-triazatetracyclo[17.2.2.13,6 .012,16]tetracosa-1(21),19,22-trien-24-yl]carbonyl}-3,3-azetidinedicarboxylate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 7 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 h / 0 - 20 °C
5: triethylamine; dmap / dichloromethane / 18 h / 0 - 20 °C
6: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane; ethyl acetate / 1 h / 20 °C / Inert atmosphere
7: N-ethyl-N,N-diisopropylamine; 2-chloro-1-methyl-pyridinium iodide / N,N-dimethyl-formamide; toluene / 3 h / 110 °C |
|
- 8
-
[ 1011479-75-6 ]
-
C39H34Cl2F3N5O11
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 8 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 h / 0 - 20 °C
5: triethylamine; dmap / dichloromethane / 18 h / 0 - 20 °C
6: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane; ethyl acetate / 1 h / 20 °C / Inert atmosphere
7: N-ethyl-N,N-diisopropylamine; 2-chloro-1-methyl-pyridinium iodide / N,N-dimethyl-formamide; toluene / 3 h / 110 °C
8: lithium hydroxide monohydrate / tetrahydrofuran; water; ethanol / 6.5 h / 0 - 20 °C |
|
- 9
-
[ 1011479-75-6 ]
-
C42H46ClF3N4O13
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 0 - 20 °C
5: triethylamine; dmap / dichloromethane / 18 h / 0 - 20 °C |
|
- 10
-
[ 1011479-75-6 ]
-
C41H48N4O13
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 0 - 20 °C
5: triethylamine; dmap / dichloromethane / 18 h / 0 - 20 °C |
|
- 11
-
[ 1011479-75-6 ]
-
C52H56N4O14
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 0 - 20 °C
5: triethylamine; dmap / dichloromethane / 18 h / 0 - 20 °C |
|
- 12
-
[ 1011479-75-6 ]
-
C35H42N4O11
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 6 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 0 - 20 °C
5: triethylamine; dmap / dichloromethane / 18 h / 0 - 20 °C
6: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane; ethyl acetate / 1 h / 20 °C / Inert atmosphere |
|
- 13
-
[ 1011479-75-6 ]
-
C31H32N4O10
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 8 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 0 - 20 °C
5: triethylamine; dmap / dichloromethane / 18 h / 0 - 20 °C
6: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane; ethyl acetate / 1 h / 20 °C / Inert atmosphere
7: N-ethyl-N,N-diisopropylamine; 2-chloro-1-methyl-pyridinium iodide / N,N-dimethyl-formamide; toluene / 2 h / 90 °C
8: lithium hydroxide; water / tetrahydrofuran; ethanol / 2 h / 20 °C |
|
- 14
-
[ 1011479-75-6 ]
-
C30H39N3O10
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 0 - 20 °C |
|
- 15
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[ 1011479-75-6 ]
-
diethyl 1-[(6S,16S,24S)-2,8,11-trioxo-9-phenyl-7,18-dioxa-3,9,12-triazatetracyclo[17.2.2.13,6 .012,16]tetracosa-1(21),19,22-trien-24-yl]carbonyl}-3,3-azetidinedicarboxylate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 7 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 0 - 20 °C
5: triethylamine; dmap / dichloromethane / 18 h / 0 - 20 °C
6: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane; ethyl acetate / 1 h / 20 °C / Inert atmosphere
7: N-ethyl-N,N-diisopropylamine; 2-chloro-1-methyl-pyridinium iodide / N,N-dimethyl-formamide; toluene / 2 h / 90 °C |
|
- 16
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[ 1011479-75-6 ]
-
C48H60ClF3N4O14Si
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C
5: triethylamine; dmap / dichloromethane / 18 h / 0 - 20 °C |
|
- 17
-
[ 1011479-75-6 ]
-
C36H53N3O11Si
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C |
|
- 18
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[ 1011479-75-6 ]
-
C42H54ClF3N4O12Si
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 6 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C
5: triethylamine; dmap / dichloromethane / 18 h / 0 - 20 °C
6: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane; ethyl acetate / 1 h / 20 °C / Inert atmosphere |
|
- 19
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[ 1011479-75-6 ]
-
C42H52ClF3N4O11Si
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 7 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C
5: triethylamine; dmap / dichloromethane / 18 h / 0 - 20 °C
6: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane; ethyl acetate / 1 h / 20 °C / Inert atmosphere
7: N-ethyl-N,N-diisopropylamine; 2-chloro-1-methyl-pyridinium iodide / N,N-dimethyl-formamide; toluene / 2 h / 90 °C |
|
- 20
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[ 1011479-75-6 ]
-
diethyl 1-[(6S,14R,16S,24S)-9-[4-chloro-3-(trifluoromethyl)phenyl]-14-hydroxy-2,8,11-trioxo-7,18-dioxa-3,9,12-triazatetracyclo[17.2.2.13,6 .012,16]tetracosa-1(21),19,22-trien-24-yl]carbonyl}-3,3-azetidinedicarboxylate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 8 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C
5: triethylamine; dmap / dichloromethane / 18 h / 0 - 20 °C
6: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane; ethyl acetate / 1 h / 20 °C / Inert atmosphere
7: N-ethyl-N,N-diisopropylamine; 2-chloro-1-methyl-pyridinium iodide / N,N-dimethyl-formamide; toluene / 2 h / 90 °C
8: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C |
|
- 21
-
[ 1011479-75-6 ]
-
C34H34ClF3N4O11
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 8 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C
5: triethylamine; dmap / dichloromethane / 18 h / 0 - 20 °C
6: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane; ethyl acetate / 1 h / 20 °C / Inert atmosphere
7: N-ethyl-N,N-diisopropylamine; 2-chloro-1-methyl-pyridinium iodide / N,N-dimethyl-formamide; toluene / 2 h / 90 °C
8: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C |
|
- 22
-
[ 1011479-75-6 ]
-
C32H30ClF3N4O11
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 9 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C
5: triethylamine; dmap / dichloromethane / 18 h / 0 - 20 °C
6: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane; ethyl acetate / 1 h / 20 °C / Inert atmosphere
7: N-ethyl-N,N-diisopropylamine; 2-chloro-1-methyl-pyridinium iodide / N,N-dimethyl-formamide; toluene / 2 h / 90 °C
8: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C
9: lithium hydroxide; water / tetrahydrofuran; ethanol / 1 h / 20 °C |
|
- 23
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[ 1011479-75-6 ]
-
diethyl 1-[(6S,14R,16S,24S)-9-[4-chloro-3-(trifluoromethyl)phenyl]-14-methoxy-2,8,11-trioxo-7,18-dioxa-3,9,12-triazatetracyclo[17.2.2.13,6 .012,16]tetracosa-1(21),19,22-trien-24-yl]carbonyl}-3,3-azetidinedicarboxylate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 7 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 0 - 20 °C
5: triethylamine; dmap / dichloromethane / 18 h / 0 - 20 °C
6: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane; ethyl acetate / 1 h / 20 °C / Inert atmosphere
7: N-ethyl-N,N-diisopropylamine; 2-chloro-1-methyl-pyridinium iodide / N,N-dimethyl-formamide; toluene / 2 h / 85 °C |
|
- 24
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[ 1011479-75-6 ]
-
C33H32ClF3N4O11
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 8 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 0 - 20 °C
5: triethylamine; dmap / dichloromethane / 18 h / 0 - 20 °C
6: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane; ethyl acetate / 1 h / 20 °C / Inert atmosphere
7: N-ethyl-N,N-diisopropylamine; 2-chloro-1-methyl-pyridinium iodide / N,N-dimethyl-formamide; toluene / 2 h / 85 °C
8: lithium hydroxide; water / tetrahydrofuran; ethanol / 9 h / 0 - 20 °C |
|
- 25
-
[ 1011479-75-6 ]
-
C43H48ClF3N4O14
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 0 - 20 °C
5: triethylamine; dmap / dichloromethane / 18 h / 0 - 20 °C |
|
- 26
-
[ 1011479-75-6 ]
-
C37H42ClF3N4O12
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 6 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 0 - 20 °C
5: triethylamine; dmap / dichloromethane / 18 h / 0 - 20 °C
6: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane; ethyl acetate / 1 h / 20 °C / Inert atmosphere |
|
- 27
-
[ 1011479-75-6 ]
-
C31H41N3O11
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 0 - 20 °C |
|
- 28
-
[ 1011479-75-6 ]
-
C43H48ClF3N4O13
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 0 °C
5: triethylamine; dmap / dichloromethane / 16 h / 0 - 20 °C |
|
- 29
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[ 1011479-75-6 ]
-
C30H39N3O11
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 0 °C |
|
- 30
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[ 1011479-75-6 ]
-
C31H41N3O10
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 0 °C |
|
- 31
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[ 1011479-75-6 ]
-
C37H42ClF3N4O11
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 6 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 0 °C
5: triethylamine; dmap / dichloromethane / 16 h / 0 - 20 °C
6: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane; ethyl acetate / 4 h / 20 °C / Inert atmosphere |
|
- 32
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[ 1011479-75-6 ]
-
C37H40ClF3N4O10
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 7 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 0 °C
5: triethylamine; dmap / dichloromethane / 16 h / 0 - 20 °C
6: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane; ethyl acetate / 4 h / 20 °C / Inert atmosphere
7: N-ethyl-N,N-diisopropylamine; 2-chloro-1-methyl-pyridinium iodide / acetonitrile / 3 h / 90 °C |
|
- 33
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[ 1011479-75-6 ]
-
C33H32ClF3N4O10
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 8 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C
4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 0 °C
5: triethylamine; dmap / dichloromethane / 16 h / 0 - 20 °C
6: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane; ethyl acetate / 4 h / 20 °C / Inert atmosphere
7: N-ethyl-N,N-diisopropylamine; 2-chloro-1-methyl-pyridinium iodide / acetonitrile / 3 h / 90 °C
8: lithium hydroxide; water / tetrahydrofuran / 1 h / 0 - 20 °C |
|
- 34
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[ 1011479-75-6 ]
-
diethyl 1-[(2S,3S)-3-hydroxypyrrolidine-2-carbonyl]azetidine-3,3-dicarboxylate trifluoroacetate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C
3: dichloromethane / 1.5 h / 0 - 20 °C |
|
- 35
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[ 1011479-75-6 ]
-
C19H30N2O8
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: dichloromethane / 1.5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 15 h / 0 - 20 °C |
|
- 36
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[ 1011479-75-6 ]
-
[ 76-05-1 ]
-
C9H15NO4*C2HF3O2
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
In dichloromethane at 20℃; for 1.5h; |
Diethyl 1 -[(2S,3S)-3-hydroxypyrrolidine-2-carbonyl]azetidine-3,3-dicarboxylate (19):
Diethyl 1 -[(2S,3S)-3-hydroxypyrrolidine-2-carbonyl]azetidine-3,3-dicarboxylate (19): At rt, a soln of 16 (4.6 g, 15.2 mmol) in CH2CI2 (80 mL) was treated with TFA (20 mL) for 90 min. The volatiles were evaporated. The residue was dissolved in toluene and concentrated to afford I7 CF3CO2H (5.9 g; contains residual TFA, purity ca 80%). Data of 17 CF3C02H: C9H15NO4 CF3CO2H (201 .2+1 14.0). FI-MS: 202.0 ([M+H]+). 1H- NMR (DMSO-de): 9.13 (br. s, NH2+); 4.33 (br. s, 4 H); 4.23 (q, J = 7.1 , 4 H); 1.22 (t, J = 7.1 , 6 H). |
- 37
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[ 24424-99-5 ]
-
diethyl azetidine-3,3-dicarboxylate hydrochloride
[ No CAS ]
-
[ 1011479-75-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 24h; |
2 Step 2: 1-(tert-butyl) 3,3-diethyl azetidine-1,3,3-tricarboxylate.
A mixture of diethyl azetidine-3,3-dicarboxylate hydrochloride (756 mg, 2.85 mmol) and Boc2O (0.82 mL, 4.00 mmol) in dioxane (12 mL) and sat. aq. NaHCO3 was stirred at rt for 24 h. The reaction mixture was diluted with sat. aq. NaHCO3(100 mL) and extracted with EtOAc (2x75 mL). The extracts were washed with brine (75 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (Hexanes/EtOAc) to afford the title compound.1H NMR (500 MHz, CDCl3) d 4.22-4.31 (m, 8H), 1.44 (s, 9H), 1.28 (t, 6H). |
| 4.02 g |
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 18h; |
58.1 Step 1.1-(tert-Butyl) 3,3-diethyl azetidine-1,3,3-tricarboxylate.
A mixture of diethyl azetidine-3,3-dicarboxylate hydrochloride (3.46 g, 14.55 mmol), di-tert-butyl dicarbonate (4.7 mL, 20.5 mmol), sat. aq. NaHCO3 (75 mL) and dioxane (75 mL) was stirred vigorously at rt for 18h. The reaction mixture was diluted with sat. aq. NaHCO3 (100 mL) and water and extracted with EtOAc (3×100 mL). The extracts were washed with brine (200 mL), dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by flash chromatography on silica gel (Hexanes/EtOAc) to give the title compound (4.02 g) as a colorless oil.1H NMR (500 MHz, CDCl3) δ ppm 4.23-4.29 (m, 8H), 1.44 (s, 9H), 1.28 (t, 6H). |
- 38
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[ 1011479-75-6 ]
-
[ 1078166-51-4 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 0 - 20℃; for 24h; Inert atmosphere; |
3 Step 3: 1-(tert-butyl) 3-ethyl 3-(hydroxymethyl)azetidine-1,3-dicarboxylate.
LiAlH(Ot-Bu)3in THF (1.0M, 4.4 mL) was added dropwise to a solution of 1-(tert-butyl) 3,3-diethyl azetidine-1,3,3-tricarboxylate (604 mg, 2.01 mmol) in dry THF (20 mL) at 0 °C under N2. The mixture was warmed to rt and stirred for 24h. The reaction mixture was diluted with EtOAc (100 mL), washed with 1 M HCl (2x50 mL) and brine (50 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (Hexanes/EtOAc) to afford the title compound. |
| 3.85 g |
With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere; |
58.2 Step 2.1-(tert-Butyl) 3-ethyl 3-(hydroxymethyl)azetidine-1,3-dicarboxylate.
LiAlH(Ot-Bu)3 (1.0 M in THF, 27.5 mL) was added dropwise by addition funnel to a solution of 1-(tert-butyl) 3,3-diethyl azetidine-1,3,3-tricarboxylate (4.02 g, 13.3 mmol) in dry THF (120 mL) at 0 °C under N2. The mixture was warmed to rt and stirred for 18h. The reaction mixture was diluted with EtOAc (150 mL) and washed with 1 M HCl (200 mL). The aqueous layer was extracted with EtOAc (150 mL) and the combined organics were washed with brine (200 mL), dried over Na2SO4, filtered and concentrated to give the title compound (3.85 g) as a colorless oil.1H NMR (500 MHz, CDCl3) δ ppm 4.26 (q, 2H), 4.15 (d, 2H), 3.95 (s, 2H), 3.81 (d, 2H), 1.45 (s, 9H), 1.32 (t, 3H). |
- 39
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[ 1011479-75-6 ]
-
1-(tert-butyl) 3-ethyl 3-(((methylsulfonyl)oxy)methyl)azetidine-1,3-dicarboxylate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere
2: triethylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere |
|
|
Multi-step reaction with 2 steps
1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 18 h / 0 - 20 °C / Inert atmosphere
2: triethylamine / dichloromethane / 2.5 h / 20 °C |
|
- 40
-
[ 1011479-75-6 ]
-
1-(tert-butyl) 3-ethyl 3-(azidomethyl)azetidine-1,3-dicarboxylate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere
2: triethylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere
3: sodium azide / N,N-dimethyl-formamide / 24 h / 50 °C / Inert atmosphere |
|
- 41
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[ 1011479-75-6 ]
-
[ 1245917-69-4 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere
2: triethylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere
3: sodium azide / N,N-dimethyl-formamide / 24 h / 50 °C / Inert atmosphere
4: palladium 10% on activated carbon; hydrogen / ethanol / 20 h |
|
- 42
-
[ 1011479-75-6 ]
-
1-(tert-butyl) 3-ethyl 3-((((benzyloxy)carbonyl)amino)methyl)azetidine-1,3-dicarboxylate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere
2: triethylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere
3: sodium azide / N,N-dimethyl-formamide / 24 h / 50 °C / Inert atmosphere
4: palladium 10% on activated carbon; hydrogen / ethanol / 20 h
5: sodium hydrogencarbonate / water; 1,4-dioxane / 96 h / 20 °C / Inert atmosphere |
|
- 43
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[ 1011479-75-6 ]
-
ethyl 3-((((benzyloxy)carbonyl)amino)methyl)azetidine-3-carboxylate trifluoroacetate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 6 steps
1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere
2: triethylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere
3: sodium azide / N,N-dimethyl-formamide / 24 h / 50 °C / Inert atmosphere
4: palladium 10% on activated carbon; hydrogen / ethanol / 20 h
5: sodium hydrogencarbonate / water; 1,4-dioxane / 96 h / 20 °C / Inert atmosphere
6: dichloromethane / 1.5 h / 20 °C |
|
- 44
-
[ 642411-11-8 ]
-
[ 1011479-75-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: hydrogen; hydrogenchloride; 20% palladium hydroxide-activated charcoal / water; 1,4-dioxane; ethanol / 144 h / 20 °C
2: sodium hydrogencarbonate / water; 1,4-dioxane / 24 h / 20 °C |
|
- 45
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[ 1011479-75-6 ]
-
4-((3-(aminomethyl)-1-((2,4-dichlorophenyl)sulfonyl)azetidin-3-yl)methoxy)-2-fluorobenzonitrile
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 11 steps
1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 18 h / 0 - 20 °C / Inert atmosphere
2: 1H-imidazole / N,N-dimethyl-formamide / 91.2 h / 20 °C / Inert atmosphere
3: dichloromethane / 2 h / 20 °C / Inert atmosphere
4: triethylamine / dichloromethane / 20 h / 20 °C / Inert atmosphere
5: triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
6: potassium carbonate / acetonitrile / 20 h / 80 °C / Inert atmosphere
7: sodium hydroxide / tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere
8: dimethylsulfide borane complex / tetrahydrofuran / 20 h / 0 - 20 °C / Inert atmosphere
9: triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere
10: sodium azide / N,N-dimethyl-formamide / 16 h / 50 °C
11: ammonium chloride; zinc / methanol / 3 h / 20 °C / Inert atmosphere |
|
- 46
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[ 1011479-75-6 ]
-
(3-((4-cyano-3-fluorophenoxy)methyl)-1-((2,4-dichlorophenyl)sulfonyl)azetidin-3-yl)methyl methanesulfonate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 9 steps
1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 18 h / 0 - 20 °C / Inert atmosphere
2: 1H-imidazole / N,N-dimethyl-formamide / 91.2 h / 20 °C / Inert atmosphere
3: dichloromethane / 2 h / 20 °C / Inert atmosphere
4: triethylamine / dichloromethane / 20 h / 20 °C / Inert atmosphere
5: triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
6: potassium carbonate / acetonitrile / 20 h / 80 °C / Inert atmosphere
7: sodium hydroxide / tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere
8: dimethylsulfide borane complex / tetrahydrofuran / 20 h / 0 - 20 °C / Inert atmosphere
9: triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere |
|
- 47
-
[ 1011479-75-6 ]
-
4-((3-(azidomethyl)-1-((2,4-dichlorophenyl)sulfonyl)azetidin-3-yl)methoxy)-2-fluorobenzonitrile
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 10 steps
1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 18 h / 0 - 20 °C / Inert atmosphere
2: 1H-imidazole / N,N-dimethyl-formamide / 91.2 h / 20 °C / Inert atmosphere
3: dichloromethane / 2 h / 20 °C / Inert atmosphere
4: triethylamine / dichloromethane / 20 h / 20 °C / Inert atmosphere
5: triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
6: potassium carbonate / acetonitrile / 20 h / 80 °C / Inert atmosphere
7: sodium hydroxide / tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere
8: dimethylsulfide borane complex / tetrahydrofuran / 20 h / 0 - 20 °C / Inert atmosphere
9: triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere
10: sodium azide / N,N-dimethyl-formamide / 16 h / 50 °C |
|
- 48
-
[ 1011479-75-6 ]
-
N-((3-((4-cyano-3-fluorophenoxy)methyl)-1-((2,4-dichlorophenyl)sulfonyl)azetidin-3-yl)methyl)acetamide
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 12 steps
1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 18 h / 0 - 20 °C / Inert atmosphere
2: 1H-imidazole / N,N-dimethyl-formamide / 91.2 h / 20 °C / Inert atmosphere
3: dichloromethane / 2 h / 20 °C / Inert atmosphere
4: triethylamine / dichloromethane / 20 h / 20 °C / Inert atmosphere
5: triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
6: potassium carbonate / acetonitrile / 20 h / 80 °C / Inert atmosphere
7: sodium hydroxide / tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere
8: dimethylsulfide borane complex / tetrahydrofuran / 20 h / 0 - 20 °C / Inert atmosphere
9: triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere
10: sodium azide / N,N-dimethyl-formamide / 16 h / 50 °C
11: ammonium chloride; zinc / methanol / 3 h / 20 °C / Inert atmosphere
12: triethylamine / dichloromethane / 2 h / 20 °C |
|
- 49
-
[ 1011479-75-6 ]
-
2-amino-N-((3-((4-cyano-3-fluorophenoxy)methyl)-1-((2,4-dichlorophenyl)sulfonyl)azetidin-3-yl)methyl)acetamide
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 13 steps
1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 18 h / 0 - 20 °C / Inert atmosphere
2: 1H-imidazole / N,N-dimethyl-formamide / 91.2 h / 20 °C / Inert atmosphere
3: dichloromethane / 2 h / 20 °C / Inert atmosphere
4: triethylamine / dichloromethane / 20 h / 20 °C / Inert atmosphere
5: triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
6: potassium carbonate / acetonitrile / 20 h / 80 °C / Inert atmosphere
7: sodium hydroxide / tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere
8: dimethylsulfide borane complex / tetrahydrofuran / 20 h / 0 - 20 °C / Inert atmosphere
9: triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere
10: sodium azide / N,N-dimethyl-formamide / 16 h / 50 °C
11: ammonium chloride; zinc / methanol / 3 h / 20 °C / Inert atmosphere
12: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 18 h / 20 °C
13: trifluoroacetic acid / dichloromethane / 2 h / 20 °C |
|
- 50
-
[ 1011479-75-6 ]
-
tert-butyl (2-(((3-((4-cyano-3-fluorophenoxy)methyl)-1-((2,4-dichlorophenyl)sulfonyl)azetidin-3-yl)methyl)amino)-2-oxoethyl)carbamate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 12 steps
1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 18 h / 0 - 20 °C / Inert atmosphere
2: 1H-imidazole / N,N-dimethyl-formamide / 91.2 h / 20 °C / Inert atmosphere
3: dichloromethane / 2 h / 20 °C / Inert atmosphere
4: triethylamine / dichloromethane / 20 h / 20 °C / Inert atmosphere
5: triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
6: potassium carbonate / acetonitrile / 20 h / 80 °C / Inert atmosphere
7: sodium hydroxide / tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere
8: dimethylsulfide borane complex / tetrahydrofuran / 20 h / 0 - 20 °C / Inert atmosphere
9: triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere
10: sodium azide / N,N-dimethyl-formamide / 16 h / 50 °C
11: ammonium chloride; zinc / methanol / 3 h / 20 °C / Inert atmosphere
12: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 18 h / 20 °C |
|
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