Alternatived Products of [ 17640-21-0 ]
Product Details of [ 17640-21-0 ]
CAS No. : | 17640-21-0 |
MDL No. : | MFCD16038497 |
Formula : |
C6H12O3
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | XYXFJNIUUWEUIJ-UHFFFAOYSA-N |
M.W : |
132.16
|
Pubchem ID : | 542192 |
Synonyms : |
|
Application In Synthesis of [ 17640-21-0 ]
* 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.
- Upstream synthesis route of [ 17640-21-0 ]
- Downstream synthetic route of [ 17640-21-0 ]
- 1
-
[ 67-63-0 ]
-
[ 625-45-6 ]
-
[ 17640-21-0 ]
Yield | Reaction Conditions | Operation in experiment |
94 - 97% |
With sulfuric acid; sodium sulfate; In cyclohexane; water; toluene; at 20 - 92℃; for 16h;Heating / reflux; |
Amounts Employed: [00150] 1 kg of extract from continuous extraction of an aqueous MEA solution of the following composition: [00151] 10.7% of methoxyacetic acid (MEA) [00152] 2.0% of isopropyl methoxyacetate [00153] 36.0% of isopropanol [00154] 38.0% of toluene [00155] 14.0% of water [00156] 0.04% of Na2SO4 [00157] Added: [00158] 40.0 g of methoxyacetic acid (MEA) [00159] 0.8 g of conc. H2SO4 (0.5 mol %) [00160] 100 ml of cyclohexane [00161] Procedure: [00162] The extract was mixed with the methoxyacetic acid, sulfuric acid and cyclohexane at room temperature (about 23 C.) and then heated to reflux. A ternary heteroazeotrope, consisting of cyclohexane/i-propanol and water (head temperature 66 C.) was distilled off through a 30 cm-long column packed with wire packing material at a still temperature of 74 to 76 C. This azeotrope was led through a phase separator which had been filled beforehand with cyclohexane and the lower aqueous phase was voided. The upper organic phase was fed back into the column. After 16 hours, the internal temperature had risen to 92 C., the head temperature in the column was 70 C. and the water content in the still was 0.07% (according to Karl-Fischer titration). [00163] According to 1H-NMR spectrum, the methoxyacetic acid had reacted to >98%. [00164] The still contents were fractionally distilled. [00165] Isol. (=isolated) yield of MEIPE: [00166] 220 g (94% of theory) [00167] Purity of the MEIPE: chem. (=chemical) purity >99,8%; d) Azeotropic Esterification of Methoxyacetic Acid/H2SO4-catalysis: Amounts Employed: [00170] 400 g (4.44 mol) of methoxyacetic acid [00171] 400 g of cyclohexane [00172] 300 g of toluene [00173] 600 g (10 mol) of isopropanol [00174] 1 g (0.01 mol) of conc. sulfuric acid (corresponds to 0.2 mol %) [00175] Procedure: [00176] Methoxyacetic acid, cyclohexane, toluene, isopropanol and sulfuric acid were initially introduced at room temperature and then heated to reflux. A ternary heteroazeotrope, consisting of cyclohexane/i-propanol and water (head temperature 66 C.) was distilled off through a 30 cm-long column packed with wire packing material at a still temperature of 74 to 76 C. This azeotrope was led through a phase separator filled beforehand with cyclohexane (contents: about 600 ml). The lower, aqueous phase in this process displaced the corresponding amount of cyclohexane, which flowed back into the reaction mixture via the column. After 6 hours, according to 1H-NMR 75% of the methoxyacetic acid had reacted and the water content in the distillation still was 0.58%. After 16 hours water no longer formed in the phase separator; the head temperature in the column had risen to 70 C. and the water content in the still was 0.01% (according to Karl-Fischer titration). According to the 1H-NMR spectrum, the methoxyacetic acid had been quantitatively reacted. [00177] The phase separator was exchanged for a column head and the still contents were fractionally distilled. [00178] Isol. yield of MEIPE: 562 g (97% of theory) [00179] Purity of the MEIPE: chem. purity: >99,8% |
56 - 90% |
With sodium sulfate; In water; toluene; at 20 - 80℃; for 10 - 35h;Heating / reflux; |
Amounts Employed: [00121] 4.4 kg of extract from continuous extraction of an aqueous MEA solution having the following composition: [00122] 12.3% of methoxyacetic acid (MEA) [00123] 38.1% of isopropanol [00124] 38.8% of toluene [00125] 10.7% of water [00126] 0.1% of Na2SO4 [00127] 15 g of acidic ion exchanger Amberlyst W 38 [00128] Procedure: [00129] The extract was treated at room temperature with the acidic ion exchanger and heated to reflux with stirring. A ternary heteroazeotrope, consisting of toluene/i-propanol and water (head temperature 76 C.) was distilled off through a 20 cm-long Vigreux column packed with wire packing material at a still temperature of 77 to 79 C. This azeotrope was led through a phase separator and the lower aqueous phase was voided. The upper organic phase was fed back into the column. After 35 hours, lower phase no longer formed in the phase separator. The water content in the still was 2.2% (according to Karl-Fischer titration). According to the 1H-NMR spectrum, the methoxyacetic acid had reacted to 85%. The ion exchanger was filtered off, the phase separator was exchanged for a column head and the still contents were fractionally distilled. [00130] Isol. yield of MEIPE: 715.5 g (90% of theory) [00131] Purity of the MEIPE: chem. purity: >99.8%; b) Ion-exchanger Catalysis, in a Bypass: Amounts Employed: [00134] 785 g of extract from continuous extraction of an aqueous MEA solution of the following composition: [00135] 12.3% of methoxyacetic acid (MEA) [00136] 38.1% of isopropanol [00137] 38.8% of toluene [00138] 10.7% of water [00139] 0.1% of Na2SO4 [00140] 50 g of acidic ion exchanger Amberlyst W 38 [00141] The apparatus can be seen in FIG. 2. [00142] Procedure: [00143] The extract was added at room temperature to a 1 1 miniplant vessel. The bottom outlet of the vessel was opened and the mixture was pumped through a column (length 30 cm, Ø: 3 cm) packed with 50 g of acidic ion exchanger Amberlyst W 38 using a membrane pump (capacity: 4.8 l/h). The heating of the miniplant vessel was increased to 140 C. and the resulting distillate was distilled off through a 20 cm-long Vigreux column (packed with wire packing material) at a still temperature of 78 to 80 C. The ternary heteroazeotrope formed, consisting of toluene/i-propanol and water (head temperature 76 C.), was led through a phase separator and the lower aqueous phase was voided. The upper organic phase was fed back into the column. In order to avoid temperature losses, the bypass, which was packed with ion exchanger, was also heated with a heating tape. On emergence from the bypass, the reaction mixture had the same temperature as in the miniplant vessel. After 10 hours, lower phase no longer formed in the phase separator. [00144] The mixture was fractionally distilled. [00145] Isol. yield of MEIPE: 82 g (56% of theory) [00146] The low yield is partly to be attributed to the fact that some of the valuable product remained in the bypass packed with ion exchanger. [00147] Purity of the MEIPE: chem. purity: 98.5% (contains toluene) |
|
for 12h;Reflux; |
General procedure: Ethyl and isopropyl esters of 2-ethoxyacetic acid were prepared by using a slightly modified method of Veld etal.42 2-Ethoxyacetic acid (14.0g, 0.136mol, 12.7mL) and p-toluenesulfonic acid (0.46g, 2.7mmol) were dissolved in ethanol or 2-propanol (250mL). The reaction mixture was refluxed for 12h after which the excess alcohol was distilled off slowly at atmospheric pressure. Then ethanol or 2-propanol (35mL) was added and subsequently distilled off slowly. The resulting crude ester was purified by distillation at atmospheric pressure through a Vigreux column to give ethyl 2-ethoxyacetate or isopropyl 2-ethoxyacetate as colorless oils. |
Reference:
[1]Patent: US6720447,2004,B1 .Location in patent: Page column 11-12
[2]European Journal of Organic Chemistry,2007,p. 5416 - 5421
[3]Journal of the American Chemical Society,2014,vol. 136,p. 5900 - 5903
[4]Tetrahedron Letters,1987,vol. 28,p. 3713 - 3714
[5]Patent: US6720447,2004,B1 .Location in patent: Page column 9-11
[6]Chemische Berichte,1934,vol. 67,p. 954
[7]Journal of Organic Chemistry,1977,vol. 42,p. 44 - 47
[8]Tetrahedron,2016,vol. 72,p. 7249 - 7255
- 2
-
[ 187737-37-7 ]
-
[ 625-45-6 ]
-
[ 17640-21-0 ]
Yield | Reaction Conditions | Operation in experiment |
|
With hydrogenchloride; pyrographite at 325℃; |
|
|
With boron trifluoride at 100 - 125℃; |
|
- 3
-
[ 6832-16-2 ]
-
[ 67-63-0 ]
-
[ 79-20-9 ]
-
[ 17639-73-5 ]
-
[ 17640-21-0 ]
-
[ 6149-45-7 ]
-
[ 17639-74-6 ]
- 4
-
[ 6832-16-2 ]
-
[ 67-63-0 ]
-
[ 17639-73-5 ]
-
[ 17640-21-0 ]
-
[ 6149-45-7 ]
-
[ 17639-74-6 ]
- 5
-
[ 6832-16-2 ]
-
[ 67-63-0 ]
-
[ 79-20-9 ]
-
[ 17639-73-5 ]
-
[ 17640-21-0 ]
-
[ 6149-45-7 ]
-
[ 17639-74-6 ]
-
[ 106-65-0 ]
- 6
-
[ 75-77-4 ]
-
[ 17640-21-0 ]
-
[ 137677-01-1 ]
-
[ 137677-01-1 ]
Yield | Reaction Conditions | Operation in experiment |
|
With lithium diisopropyl amide In tetrahydrofuran at -78℃; |
|
- 7
-
[ 17640-21-0 ]
-
[ 827-97-4 ]
-
(1R,1'R)-N,N'-(1,4-phenylene)bis(ethane-1,1'-diyl)bis(2-methoxyacetamide)
[ No CAS ]
-
(1S,1'S)-N,N'-(1,4-phenylene)bis(ethane-1,1'-diyl)bis(2-methoxyacetamide)
[ No CAS ]
-
(1S,1'R)-N,N'-(1,4-phenylene)bis(ethane-1,1'-diyl)bis(2-methoxyacetamide)
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With Novozym 435; 2,4-dimethyl-3-pentanol; sodium carbonate In toluene at 100℃; for 26h; Title compound not separated from byproducts.; |
|
- 8
-
[ 17640-21-0 ]
-
[ 618-36-0 ]
-
[ 162929-44-4 ]
Yield | Reaction Conditions | Operation in experiment |
92% |
With sodium carbonate In toluene at 70℃; for 6h; Inert atmosphere; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; |
|
68% |
With Novozym 435; 2,4-dimethyl-3-pentanol; sodium carbonate In toluene at 100℃; for 26h; |
|
74 %Chromat. |
With Candida antarctica lipase B; 2,4-dimethyl-3-pentanol; C70H58O14Ru2; sodium carbonate In toluene at 90℃; for 24h; optical yield given as %ee; |
|
> 99.9 % ee |
With Candida antarctica lipase B In toluene at 30℃; for 1h; Resolution of racemate; Enzymatic reaction; enantioselective reaction; |
Kinetic resolution of rac-1 by various CaLB biocatalysts using 2.0 equiv of ethyl and isopropyl esters of acetic and 2-ethoxyacetic acid as acyl donors (Table 1)
General procedure: In a screw cap reaction vessel were added a mixture of dry toluene (2.0mL), rac-1 (94mg, 0.385M) and an acyl donor (ethyl acetate, isopropyl acetate, ethyl 2-ethoxyacetate or isopropyl 2-ethoxyacetate: 2equiv, 0.770M) and the immobilized CaLB biocatalyst (N435, T2-150, SGA10D, G250P, G250O or PAP31A: 50.0mg). The reaction mixtures were shaken (350rpm) at 30°C. The reactions were monitored by taking samples and analyzed by TLC and GC as described in Section 4.2. |
Reference:
[1]Location in patent: experimental part
Kim, Yunwoong; Park, Jaiwook; Kim, Mahn-Joo
[Tetrahedron Letters, 2010, vol. 51, # 42, p. 5581 - 5584]
[2]Veld, Martijn A. J.; Hult, Karl; Palmans, Anja R. A.; Meijer
[European Journal of Organic Chemistry, 2007, # 32, p. 5416 - 5421]
[3]Location in patent: experimental part
Thalen, Lisa K.; Baeckvall
[Beilstein Journal of Organic Chemistry, 2010, vol. 6, p. 823 - 829]
[4]Oláh, Márk; Boros, Zoltán; Hornyánszky, Gábor; Poppe, László
[Tetrahedron, 2016, vol. 72, # 46, p. 7249 - 7255]
- 9
-
[ 17640-21-0 ]
-
[ 42070-98-4 ]
-
[ 296236-17-4 ]
Yield | Reaction Conditions | Operation in experiment |
94% |
With sodium carbonate In toluene at 70℃; for 6h; Inert atmosphere; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; |
|
73% |
With Novozym 435; 2,4-dimethyl-3-pentanol; sodium carbonate In toluene at 100℃; for 26h; |
|
Reference:
[1]Location in patent: experimental part
Kim, Yunwoong; Park, Jaiwook; Kim, Mahn-Joo
[Tetrahedron Letters, 2010, vol. 51, # 42, p. 5581 - 5584]
[2]Veld, Martijn A. J.; Hult, Karl; Palmans, Anja R. A.; Meijer
[European Journal of Organic Chemistry, 2007, # 32, p. 5416 - 5421]
- 10
-
[ 17640-21-0 ]
-
[ 24358-62-1 ]
-
N-[(1R)-1-(4-bromophenyl)ethyl]-2-methoxyacetamide
[ No CAS ]
- 11
-
[ 17640-21-0 ]
-
[ 34698-41-4 ]
-
N-[(1R)-2,3-dihydro-1H-inden-1-yl]-2-methoxyacetamide
[ No CAS ]
- 12
-
[ 17640-21-0 ]
-
[ 42882-31-5 ]
-
(R)-2-methoxy-N-[1-(naphthalen-1-yl)]acetamide
[ No CAS ]
- 13
-
[ 693-16-3 ]
-
[ 17640-21-0 ]
-
(R)-2-methoxy-N-(octan-2-yl)acetamide
[ No CAS ]
-
(S)-2-methoxy-N-(octan-2-yl)acetamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With Novozym 435; 2,4-dimethyl-3-pentanol; sodium carbonate In toluene at 100℃; for 26h; Title compound not separated from byproducts.; |
|
- 14
-
1,1'-(1,3-phenylene)bisethanamine
[ No CAS ]
-
[ 17640-21-0 ]
-
(1R,1'R)-N,N'-(1,3-phenylene)bis(ethane-1,1'-diyl)bis(2-methoxyacetamide)
[ No CAS ]
-
(1S,1'S)-N,N'-(1,3-phenylene)bis(ethane-1,1'-diyl)bis(2-methoxyacetamide)
[ No CAS ]
-
(1S,1'R)-N,N'-(1,3-phenylene)bis(ethane-1,1'-diyl)bis(2-methoxyacetamide)
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With Novozym 435; 2,4-dimethyl-3-pentanol; sodium carbonate In toluene at 100℃; for 26h; Title compound not separated from byproducts.; |
|
- 15
-
[ 96-34-4 ]
-
[ 17640-21-0 ]
Yield | Reaction Conditions | Operation in experiment |
74% |
With sodium methylate In methanol; isopropyl alcohol |
1 Isopropyl Methoxyacetate
Example 1 Isopropyl Methoxyacetate 434.1 g (4.0 mol) of methyl chloroacetate are initially introduced and stirred at 25° C. 756.3 g (4.2 mol) of 30% strength sodium methoxide solution are added dropwise in the course of 2.5 h such that a reaction temperature of 65° C. is not exceeded. After the addition, stirring is continued at reflux temperature for a further 3 h. 436.0 g of methanol are then removed from the reaction mixture by distillation. 480.8 g (8 mol) of isopropanol are added to the residue and the mixture is heated under reflux. In the course of this, methanol is removed via a 0.5 m long Multifil column at a reflux ratio of approximately 1:1 (244.4 g of distillate). After 6.5 h, the conversion of the methyl methoxyacetate to the isopropyl methoxyacetate is >98%. After cooling, the reaction mixture is concentrated to dryness on a rotary evaporator at a maximum bath temperature of 120° C. and a pressure of <15 mbar. A residue of 274.3 g and a distillate of 668.0 g are obtained. The distillate is fractionated through a 0.5 m long Multifil column. Isopropyl methoxyacetate is obtained as the main fraction (390.6 g, yield 74%) with a purity of >99%, a chlorine content of 10 ppm and a water content of <0.05%. |
- 16
-
[ 17640-21-0 ]
-
[ 143589-82-6 ]
-
[ 917911-58-1 ]
-
[ 917911-59-2 ]
Yield | Reaction Conditions | Operation in experiment |
1: 96%
2: 100% |
Stage #1: isopropyl methoxyacetate; 1(R,S)-(p-tert-butoxyphenyl)ethylamine With novozyme 435 at 20 - 35℃;
Stage #2: With sulfuric acid In toluene |
|
- 17
-
1-(3-tert-butoxyphenyl)ethylamine
[ No CAS ]
-
[ 17640-21-0 ]
-
(S)-1-(3-tert-butoxyphenyl)ethylamine
[ No CAS ]
-
[ 917911-62-7 ]
Yield | Reaction Conditions | Operation in experiment |
1: 99 - 99.1 % ee
2: 94% |
Stage #1: 1-(3-tert-butoxyphenyl)ethylamine; isopropyl methoxyacetate With novozyme 435 at 20℃; for 16h;
Stage #2: With sulfuric acid In toluene
Stage #3: With sodium hydroxide In water; toluene |
|
- 18
-
[ 767334-91-8 ]
-
[ 17640-21-0 ]
-
[ 767351-03-1 ]
-
[ 1062068-83-0 ]
Yield | Reaction Conditions | Operation in experiment |
|
With Candida antacrtica lipase B at 20℃; Enzymatic reaction; optical yield given as %ee; |
|
- 19
-
[ 3850-30-4 ]
-
[ 17640-21-0 ]
-
[ 424824-68-0 ]
-
(S)-1,2,2-trimethylpropylamine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With Candida antacrtica lipase B at 20℃; Enzymatic reaction; optical yield given as %ee; |
|
- 20
-
[ 13205-58-8 ]
-
[ 17640-21-0 ]
-
[ 869278-88-6 ]
-
[ 1062068-77-2 ]
Yield | Reaction Conditions | Operation in experiment |
|
With Candida antacrtica lipase B at 20℃; Enzymatic reaction; optical yield given as %ee; |
|
- 21
-
[ 17640-21-0 ]
-
[ 34698-41-4 ]
-
N-[(1R)-2,3-dihydro-1H-inden-1-yl]-2-methoxyacetamide
[ No CAS ]
-
[ 10277-74-4 ]
Yield | Reaction Conditions | Operation in experiment |
44%; 39% |
With Novozym 435; at 23℃; for 2h;Molecular sieve; Enzymatic reaction; |
General procedure: One of the amines rac-1a-i (2 mmol) and isopropyl methoxyacetate (2 mmol) were added into a reaction vessel containing Novozym 435 (25 mg) and molecular sieves (4 A, 50 mg). The reaction mixture was shaken (170 rpm) at room temperature (23 C) if not otherwise stated. The reaction was stopped by filtering off the enzyme at (50 +/- 0.5)% conversion. Isolation of the products was performed by silica gel chromatography using a mixture of hexane and ethylacetate and/or mixture of dichloromethane and methanol as eluent. |
- 22
-
[ 17640-21-0 ]
-
[ 42882-31-5 ]
-
(R)-2-methoxy-N-[1-(naphthalen-1-yl)]acetamide
[ No CAS ]
-
[ 10420-89-0 ]
Yield | Reaction Conditions | Operation in experiment |
93%; 92% |
With immobilized lipase B from Candida antarctica (Novozyme 435); In diethyl ether; |
The racemate resolution of 1-(1-naphthyl)ethylamine was carried out as described by K. Ditrich (Synthesis 2008, 14; 2283-2287). 1-(1-Naphthyl)ethylamine (17.2 g, 0.1 mol) and isopropyl methoxyacetate (19.8 g, 0.15 mol) were dissolved in diethyl ether (400 ml). After addition of immobilized lipase B from Candida antarctica (Novozyme 435) (1 g), the turbid solution was stirred overnight at room temperature (30 rpm). The progress of the reaction was monitored by means of chiral HPLC. The reaction was stopped when an ee of 99.5% for the unreacted S-enantiomer and of 99.1% for the amide of the R-enantiomer was reached. Solid reaction residues were removed by filtration and washed with diethyl ether (50 ml). The combined filtrates were admixed with 5% strength aqueous HCl (50 ml) while stirring. After phase separation, the organic phase was washed with water (100 ml). The combined aqueous phases were reextracted with diethyl ether (3×70 ml) and the combined organic extracts were dried over sodium sulfate. After evaporation of the solvent and removal of unreacted isopropyl methoxyacetate by distillation, the amide of the R-enantiomer was obtained in the form of colorless crystals in a yield of 93%. An optically pure sample having a melting point of 80 C. could be obtained by recrystallization from cyclohexane. The combined aqueous extracts were made alkaline (pH 13) by addition of 50% strength aqueous NaOH while cooling in an ice bath. Diethyl ether (75 ml) was subsequently added and the phases were separated. The aqueous phase was extracted with diethyl ether (2×75 ml) and the combined extracts were dried over sodium sulfate. After evaporation of the solvent and purification by distillation, the S-enantiomer which remained was obtained in a yield of 92%. |
48%; 45% |
With Novozym 435; at 47℃;Molecular sieve; Enzymatic reaction; |
General procedure: One of the amines rac-1a-i (2 mmol) and isopropyl methoxyacetate (2 mmol) were added into a reaction vessel containing Novozym 435 (25 mg) and molecular sieves (4 A, 50 mg). The reaction mixture was shaken (170 rpm) at room temperature (23 C) if not otherwise stated. The reaction was stopped by filtering off the enzyme at (50 +/- 0.5)% conversion. Isolation of the products was performed by silica gel chromatography using a mixture of hexane and ethylacetate and/or mixture of dichloromethane and methanol as eluent. |
- 23
-
[ 17640-21-0 ]
-
[ 42070-98-4 ]
-
[ 296236-17-4 ]
-
[ 27298-98-2 ]
Yield | Reaction Conditions | Operation in experiment |
45%; 45% |
With Novozym 435; at 23℃; for 3h;Molecular sieve; Enzymatic reaction; |
General procedure: One of the amines rac-1a-i (2 mmol) and isopropyl methoxyacetate (2 mmol) were added into a reaction vessel containing Novozym 435 (25 mg) and molecular sieves (4 A, 50 mg). The reaction mixture was shaken (170 rpm) at room temperature (23 C) if not otherwise stated. The reaction was stopped by filtering off the enzyme at (50 +/- 0.5)% conversion. Isolation of the products was performed by silica gel chromatography using a mixture of hexane and ethylacetate and/or mixture of dichloromethane and methanol as eluent. |
- 24
-
[ 17640-21-0 ]
-
[ 2941-20-0 ]
-
[ 933065-32-8 ]
-
[ 3789-59-1 ]
Yield | Reaction Conditions | Operation in experiment |
1: 41%
2: 45% |
With Novozym 435 at 23℃; for 24h; Molecular sieve; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; |
4.3. Preparative-scale solvent-free kinetic resolution of rac-1a-i
General procedure: One of the amines rac-1a-i (2 mmol) and isopropyl methoxyacetate (2 mmol) were added into a reaction vessel containing Novozym 435 (25 mg) and molecular sieves (4 Å, 50 mg). The reaction mixture was shaken (170 rpm) at room temperature (23 °C) if not otherwise stated. The reaction was stopped by filtering off the enzyme at (50 +/- 0.5)% conversion. Isolation of the products was performed by silica gel chromatography using a mixture of hexane and ethylacetate and/or mixture of dichloromethane and methanol as eluent. |
|
With Candida antacrtica lipase B at 20℃; Enzymatic reaction; optical yield given as %ee; |
|
Reference:
[1]Location in patent: experimental part
Paeivioe, Mari; Perkioe, Paeivi; Kanerva, Liisa T.
[Tetrahedron Asymmetry, 2012, vol. 23, # 3-4, p. 230 - 236]
[2]Location in patent: experimental part
Ditrich, Klaus
[Synthesis, 2008, # 14 SPEC. ISS., p. 2283 - 2287]
- 25
-
[ 17640-21-0 ]
-
[ 24358-62-1 ]
-
N-[(1R)-1-(4-bromophenyl)ethyl]-2-methoxyacetamide
[ No CAS ]
-
[ 27298-97-1 ]
- 26
-
[ 17640-21-0 ]
-
[ 89981-75-9 ]
-
N-[(1R)-1-(2,4-dichlorophenyl)ethyl]-2-methoxyacetamide
[ No CAS ]
-
[ 133492-69-0 ]
Yield | Reaction Conditions | Operation in experiment |
|
With Candida antacrtica lipase B at 20℃; Enzymatic reaction; optical yield given as %ee; |
|
- 27
-
[ 17640-21-0 ]
-
[ 618-36-0 ]
-
[ 2627-86-3 ]
-
[ 162929-44-4 ]
Yield | Reaction Conditions | Operation in experiment |
|
With Candida antartica lipase B at 20℃; Enzymatic reaction; optical yield given as %ee; |
|
|
With Novozym 435 at 23℃; for 4h; Molecular sieve; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; |
4.2. Kinetic resolution of rac-1a in toluene and under solvent-free conditions
General procedure: One of the acyl donors (0.2 M; isopropyl acetate, isopropyl butanoate. ethyl or isopropyl methoxyacetate) was added into a reaction vessel containing molecular sieves (4 Å, 50 mg) and the suspension of Novozym 435 (10 mg mL-1), toluene (1 mL) and rac-1a (0.1 M), or rac-1a (2 mmol) and an acyl donor (2 mmol) were added into a reaction vessel containing Novozym 435 (10-50 mg) and molecular sieves (4 Å, 50 mg). The reaction mixture was shaken (170 rpm) at room temperature (23 °C) or at 47 °C. The reactions were monitored by taking samples which were derivatized with acetic or propionic anhydride and analyzed by GC or HPLC. |
|
With lipase B from Candida antarctica immobilized on acrylic beads In toluene at 30℃; for 8h; Resolution of racemate; Enzymatic reaction; enantioselective reaction; |
|
Reference:
[1]Location in patent: experimental part
Ditrich, Klaus
[Synthesis, 2008, # 14 SPEC. ISS., p. 2283 - 2287]
[2]Location in patent: experimental part
Paeivioe, Mari; Perkioe, Paeivi; Kanerva, Liisa T.
[Tetrahedron Asymmetry, 2012, vol. 23, # 3-4, p. 230 - 236]
[3]Oláh, Márk; Kovács, Dániel; Katona, Gabriel; Hornyánszky, Gábor; Poppe, László
[Tetrahedron, 2018, vol. 74, # 27, p. 3663 - 3670]
- 28
-
[ 17640-21-0 ]
-
[ 93192-72-4 ]
-
[ 314081-28-2 ]
-
[ 1062068-74-9 ]
Yield | Reaction Conditions | Operation in experiment |
|
With Candida antacrtica lipase B at 20℃; Enzymatic reaction; optical yield given as %ee; |
|
- 29
-
[ 2217-40-5 ]
-
[ 17640-21-0 ]
-
2-methoxy-N-((R)-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
97% |
With sodium carbonate In toluene at 70℃; for 6h; Inert atmosphere; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; |
|
- 30
-
[ 53981-38-7 ]
-
[ 17640-21-0 ]
-
[ 730980-58-2 ]
- 31
-
[ 17640-21-0 ]
-
[ 6298-96-0 ]
-
2-methoxy-N-((R)-1-(4-methoxyphenyl)ethyl)acetamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
88% |
With sodium carbonate In toluene at 70℃; for 6h; Inert atmosphere; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; |
|
- 32
-
[ 17640-21-0 ]
-
[ 2941-20-0 ]
-
C13H19NO2
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
97% |
With sodium carbonate In toluene at 70℃; for 12h; Inert atmosphere; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; |
|
- 33
-
[ 17640-21-0 ]
-
[ 618-36-0 ]
-
2-methoxy-N-[(S)-1-phenylethyl]acetamide
[ No CAS ]
-
[ 162929-44-4 ]
Yield | Reaction Conditions | Operation in experiment |
|
With Candida antarctica lipase B; 2,4-dimethyl-3-pentanol; C70H58O14Ru2; sodium carbonate In toluene at 90℃; for 72h; optical yield given as %ee; |
|
- 34
-
[ 2217-40-5 ]
-
[ 17640-21-0 ]
-
2-methoxy-N-((R)-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide
[ No CAS ]
-
[ 23357-52-0 ]
Yield | Reaction Conditions | Operation in experiment |
1: 34%
2: 45% |
With Novozym 435 at 23℃; for 2h; Molecular sieve; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; |
4.3. Preparative-scale solvent-free kinetic resolution of rac-1a-i
General procedure: One of the amines rac-1a-i (2 mmol) and isopropyl methoxyacetate (2 mmol) were added into a reaction vessel containing Novozym 435 (25 mg) and molecular sieves (4 Å, 50 mg). The reaction mixture was shaken (170 rpm) at room temperature (23 °C) if not otherwise stated. The reaction was stopped by filtering off the enzyme at (50 +/- 0.5)% conversion. Isolation of the products was performed by silica gel chromatography using a mixture of hexane and ethylacetate and/or mixture of dichloromethane and methanol as eluent. |
- 35
-
[ 17640-21-0 ]
-
[ 22374-89-6 ]
-
(R)-N-(1-methyl-3-phenylpropyl)-2-methoxyacetamide
[ No CAS ]
-
[ 4187-57-9 ]
Yield | Reaction Conditions | Operation in experiment |
1: 45%
2: 48% |
With Novozym 435 at 23℃; for 1h; Molecular sieve; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; |
4.3. Preparative-scale solvent-free kinetic resolution of rac-1a-i
General procedure: One of the amines rac-1a-i (2 mmol) and isopropyl methoxyacetate (2 mmol) were added into a reaction vessel containing Novozym 435 (25 mg) and molecular sieves (4 Å, 50 mg). The reaction mixture was shaken (170 rpm) at room temperature (23 °C) if not otherwise stated. The reaction was stopped by filtering off the enzyme at (50 +/- 0.5)% conversion. Isolation of the products was performed by silica gel chromatography using a mixture of hexane and ethylacetate and/or mixture of dichloromethane and methanol as eluent. |
40% |
With lipase B from Candida antarctica immobilized on acrylic beads In toluene at 30℃; for 8h; Resolution of racemate; Enzymatic reaction; enantioselective reaction; |
4.4. Kinetic resolution of racemic amines rac-1a-i in shake flask
General procedure: Into a screw cap reaction vial were added a mixture of dry toluene (1.0 mL), immobilized CaLB enzyme (15.0 mg, CaLB-CV-T2-150), the corresponding racemic amine rac-1a-d (0.778 mmol) and the corresponding isopropyl 2-alkoxyacetate 2A-D (1.0 equiv., 0.778 mmol). The reaction mixture was shaken (750 rpm) at 30 °C and monitored by taking samples (20 mL) after different reaction times (0.25, 0.5, 1, 2, 3, 4, 6, 8 h). After 8 h, the reactions were worked up. |
Reference:
[1]Location in patent: experimental part
Paeivioe, Mari; Perkioe, Paeivi; Kanerva, Liisa T.
[Tetrahedron Asymmetry, 2012, vol. 23, # 3-4, p. 230 - 236]
[2]Oláh, Márk; Kovács, Dániel; Katona, Gabriel; Hornyánszky, Gábor; Poppe, László
[Tetrahedron, 2018, vol. 74, # 27, p. 3663 - 3670]
- 36
-
[ 17640-21-0 ]
-
[ 403-40-7 ]
-
[ 1373832-85-9 ]
-
[ 66399-30-2 ]
Yield | Reaction Conditions | Operation in experiment |
1: 37%
2: 39% |
With Novozym 435 at 23℃; for 3h; Molecular sieve; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; |
4.3. Preparative-scale solvent-free kinetic resolution of rac-1a-i
General procedure: One of the amines rac-1a-i (2 mmol) and isopropyl methoxyacetate (2 mmol) were added into a reaction vessel containing Novozym 435 (25 mg) and molecular sieves (4 Å, 50 mg). The reaction mixture was shaken (170 rpm) at room temperature (23 °C) if not otherwise stated. The reaction was stopped by filtering off the enzyme at (50 +/- 0.5)% conversion. Isolation of the products was performed by silica gel chromatography using a mixture of hexane and ethylacetate and/or mixture of dichloromethane and methanol as eluent. |
- 37
-
[ 17640-21-0 ]
-
[ 35588-60-4 ]
-
[ 192210-96-1 ]
-
[ 4187-56-8 ]
Yield | Reaction Conditions | Operation in experiment |
47%; 46% |
With Novozym 435; at 23℃; for 2h;Molecular sieve; Enzymatic reaction; |
General procedure: One of the amines rac-1a-i (2 mmol) and isopropyl methoxyacetate (2 mmol) were added into a reaction vessel containing Novozym 435 (25 mg) and molecular sieves (4 A, 50 mg). The reaction mixture was shaken (170 rpm) at room temperature (23 C) if not otherwise stated. The reaction was stopped by filtering off the enzyme at (50 +/- 0.5)% conversion. Isolation of the products was performed by silica gel chromatography using a mixture of hexane and ethylacetate and/or mixture of dichloromethane and methanol as eluent. |
- 38
-
[ 17640-21-0 ]
-
[ 61894-99-3 ]
-
[ 1374648-20-0 ]
-
[ 116650-34-1 ]
- 39
-
[ 38870-89-2 ]
-
[ 67-63-0 ]
-
[ 17640-21-0 ]
Yield | Reaction Conditions | Operation in experiment |
|
In neat (no solvent) at 120℃; for 0.0833333h; |
|
- 40
-
[ 17640-21-0 ]
-
[ 618-36-0 ]
-
[ 21003-56-5 ]
-
[ 162929-44-4 ]
Yield | Reaction Conditions | Operation in experiment |
1: 65%
2: 10% |
With 1-hydroxytetraphenyl-cyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II) In diethylene glycol dimethyl ether at 105℃; for 24h; Enzymatic reaction; |
3.1 Reactor setup
General procedure: General experimental conditions and results on the DKR reactions are collected in Table2. First, 110mg (1mol%) of the Shvo's catalyst, 70ml of the corresponding glyme, racemic 1-(aryl)ethylamine and the corresponding acyl donor were placed in a three-necked 100ml round-bottom flask, equipped with a thermometer, a magnetic stirrer bar, a capillar and a Soxhlet head (50ml) with a reflux condenser. The enzyme (Novozyme 435) was packed in 4 porous polyethylene bags, 50mg in each. In the case of the slower reacting 1-(naphthyl)ethylamine, 6 bags containing 300mg of enzyme in total were utilized. The bags containing the enzyme were placed into an extraction chamber of the Soxhlet extractor together with 5mm glass beads. In this way the “dead volume” of the Soxhlet extractor was reduced to approximately 20ml. Disposable thermo-sensors were placed between the enzyme bags. If desired, with proper construction of the reflux condenser, a thermometer could also be inserted into the glass beads. The outlet of the reflux condenser was connected to an inlet of a membrane pump equipped with vacuum control unit. The argon inlet was connected to the capillar and to the gas inlet of the pump. We recommend the incorporation of a 1-2l buffer flask between the apparatus and the vacuum pump for controlling the vacuum oscillation. The use of Teflon thermostable grease for the hot joints is likewise recommended. The side arm of the extractor should be thermally insulated. Loops of rubber tubing with cooling water circulation can be applied around the extraction chamber for additional cooling of the enzyme. |
- 41
-
[ 17640-21-0 ]
-
[ 403-40-7 ]
-
[ 1373832-85-9 ]
Yield | Reaction Conditions | Operation in experiment |
65% |
With 1-hydroxytetraphenyl-cyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II) In diethylene glycol dimethyl ether at 105℃; for 48h; Enzymatic reaction; |
3.1 Reactor setup
General procedure: General experimental conditions and results on the DKR reactions are collected in Table2. First, 110mg (1mol%) of the Shvo's catalyst, 70ml of the corresponding glyme, racemic 1-(aryl)ethylamine and the corresponding acyl donor were placed in a three-necked 100ml round-bottom flask, equipped with a thermometer, a magnetic stirrer bar, a capillar and a Soxhlet head (50ml) with a reflux condenser. The enzyme (Novozyme 435) was packed in 4 porous polyethylene bags, 50mg in each. In the case of the slower reacting 1-(naphthyl)ethylamine, 6 bags containing 300mg of enzyme in total were utilized. The bags containing the enzyme were placed into an extraction chamber of the Soxhlet extractor together with 5mm glass beads. In this way the “dead volume” of the Soxhlet extractor was reduced to approximately 20ml. Disposable thermo-sensors were placed between the enzyme bags. If desired, with proper construction of the reflux condenser, a thermometer could also be inserted into the glass beads. The outlet of the reflux condenser was connected to an inlet of a membrane pump equipped with vacuum control unit. The argon inlet was connected to the capillar and to the gas inlet of the pump. We recommend the incorporation of a 1-2l buffer flask between the apparatus and the vacuum pump for controlling the vacuum oscillation. The use of Teflon thermostable grease for the hot joints is likewise recommended. The side arm of the extractor should be thermally insulated. Loops of rubber tubing with cooling water circulation can be applied around the extraction chamber for additional cooling of the enzyme. |
- 42
-
[ 17640-21-0 ]
-
C16H24O6
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C
1.2: 1.25 h / -78 °C
2.1: titanium(IV) dichlorodiisopropylate / dichloromethane / 16 h / -20 °C / Inert atmosphere
3.1: zinc; acetic acid; water / toluene / 16 h / 20 °C |
|
- 43
-
[ 17640-21-0 ]
-
[ 1583259-34-0 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C
1.2: 1.25 h / -78 °C
2.1: titanium(IV) dichlorodiisopropylate / dichloromethane / 16 h / -20 °C / Inert atmosphere |
|
- 44
-
[ 17640-21-0 ]
-
[ 18162-48-6 ]
-
[ 1583259-19-1 ]
Yield | Reaction Conditions | Operation in experiment |
95% |
Stage #1: isopropyl methoxyacetate With potassium hexamethylsilazane In tetrahydrofuran at -78℃; for 0.75h;
Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran at -78℃; for 1.25h; |
|
- 45
-
[ 51872-03-8 ]
-
[ 17640-21-0 ]
-
(R)-2-methoxy-N-[1-(6-methoxynaphth-2-yl)ethyl]acetamide
[ No CAS ]
-
1-(6-methoxynaphth-2-yl)ethylamine hydrochloride
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: 1-(6-methoxynaphthalen-2-yl)ethylamine hydrochloride With sodium hydroxide In tert-butyl methyl ether for 0.25h; Resolution of racemate;
Stage #2: isopropyl methoxyacetate In tert-butyl methyl ether at 42 - 45℃; for 40h; Resolution of racemate; Enzymatic reaction;
Stage #3: With hydrogenchloride In water at 0℃; |
|
Reference:
[1]Scheidt, Thomas; Land, Henrik; Anderson, Mattias; Chen, Yujie; Berglund, Per; Yi, Dong; Fessner, Wolf-Dieter
[Advanced Synthesis and Catalysis, 2015, vol. 357, # 8, p. 1721 - 1731]
- 46
-
[ 253168-94-4 ]
-
[ 17640-21-0 ]
-
(S)-N-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)-ethyl)-2-methoxyacetamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
45% |
With Novozym 435; at 105℃; for 37h;Enzymatic reaction;Catalytic behavior; |
50 mg of Novozym 435, 20 ml of CPME and 0.121 ml (8.757 mmol) of isopropylmethoxy acetate Sab are added to 0.342 g (1.25 1 mmd) of the racemic amine (rac)-1 and the reaction mixture is stirred at 105C for 37 h. The resulting mixture containing 47% of the respective amide 2ba is filtered, concentrated at a reduced pressure on an evaporator and the product is isolated with the use of column chromatography on silica gel (an ethyl acetate/hexane mixture as the mobile phase). The process provides 194 mg (45%) of thecrystalline compound (8)-2ba with the chiral purity of ee 95% and chemical purity of 99.2% (HPLC). |
- 47
-
[ 17640-21-0 ]
-
[ 108-24-7 ]
-
[ 618-36-0 ]
-
[ 19144-86-6 ]
-
[ 162929-44-4 ]
Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: isopropyl methoxyacetate; rac-methylbenzylamine With lipase B from Candida antarctica immobilized on acrylic beads In toluene at 30℃; for 8h; Resolution of racemate; Enzymatic reaction;
Stage #2: acetic anhydride In ethanol; toluene at 60℃; enantioselective reaction; |
|
- 48
-
[ 17640-21-0 ]
-
[ 22374-89-6 ]
-
[ 108-24-7 ]
-
(R)-N-(1-methyl-3-phenylpropyl)-2-methoxyacetamide
[ No CAS ]
-
N-((S)-4-phenylbutan-2-yl)acetamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
40% |
Stage #1: isopropyl methoxyacetate; (RS)-1-methyl-3-phenylpropylamine With lipase B from Candida antarctica immobilized on acrylic beads In toluene at 30℃; for 8h; Resolution of racemate; Enzymatic reaction;
Stage #2: acetic anhydride In ethanol; toluene at 60℃; enantioselective reaction; |
4.4. Kinetic resolution of racemic amines rac-1a-i in shake flask
General procedure: Into a screw cap reaction vial were added a mixture of dry toluene (1.0 mL), immobilized CaLB enzyme (15.0 mg, CaLB-CV-T2-150), the corresponding racemic amine rac-1a-d (0.778 mmol) and the corresponding isopropyl 2-alkoxyacetate 2A-D (1.0 equiv., 0.778 mmol). The reaction mixture was shaken (750 rpm) at 30 °C and monitored by taking samples (20 mL) after different reaction times (0.25, 0.5, 1, 2, 3, 4, 6, 8 h). After 8 h, the reactions were worked up. |
- 49
-
[ 17640-21-0 ]
-
[ 108-24-7 ]
-
[ 123-82-0 ]
-
[ 1056469-59-0 ]
-
S-(+)-2-Acetylaminoheptan
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
40% |
|
General procedure: Into a screw cap reaction vial were added a mixture of dry toluene (1.0 mL), immobilized CaLB enzyme (15.0 mg, CaLB-CV-T2-150), the corresponding racemic amine rac-1a-d (0.778 mmol) and the corresponding isopropyl 2-alkoxyacetate 2A-D (1.0 equiv., 0.778 mmol). The reaction mixture was shaken (750 rpm) at 30 C and monitored by taking samples (20 mL) after different reaction times (0.25, 0.5, 1, 2, 3, 4, 6, 8 h). After 8 h, the reactions were worked up. |
- 50
-
[ 17640-21-0 ]
-
[ 108-24-7 ]
-
[ 37143-54-7 ]
-
[ 437981-28-7 ]
-
(R)-2-methoxy-N-(1-methoxypropan-2-yl)acetamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
30% |
Stage #1: isopropyl methoxyacetate; methoxyisopropylamine With lipase B from Candida antarctica immobilized on acrylic beads In toluene at 30℃; for 8h; Resolution of racemate; Enzymatic reaction;
Stage #2: acetic anhydride In ethanol; toluene at 60℃; enantioselective reaction; |
4.4. Kinetic resolution of racemic amines rac-1a-i in shake flask
General procedure: Into a screw cap reaction vial were added a mixture of dry toluene (1.0 mL), immobilized CaLB enzyme (15.0 mg, CaLB-CV-T2-150), the corresponding racemic amine rac-1a-d (0.778 mmol) and the corresponding isopropyl 2-alkoxyacetate 2A-D (1.0 equiv., 0.778 mmol). The reaction mixture was shaken (750 rpm) at 30 °C and monitored by taking samples (20 mL) after different reaction times (0.25, 0.5, 1, 2, 3, 4, 6, 8 h). After 8 h, the reactions were worked up. |
- 51
-
[ 17640-21-0 ]
-
[ 123-82-0 ]
-
[ 123-82-0 ]
-
[ 1056469-59-0 ]
Yield | Reaction Conditions | Operation in experiment |
40% |
With lipase B from Candida antarctica immobilized on acrylic beads; In toluene; at 30℃; for 8h;Resolution of racemate; Enzymatic reaction; |
General procedure: Into a screw cap reaction vial were added a mixture of dry toluene (1.0 mL), immobilized CaLB enzyme (15.0 mg, CaLB-CV-T2-150), the corresponding racemic amine rac-1a-d (0.778 mmol) and the corresponding isopropyl 2-alkoxyacetate 2A-D (1.0 equiv., 0.778 mmol). The reaction mixture was shaken (750 rpm) at 30 C and monitored by taking samples (20 mL) after different reaction times (0.25, 0.5, 1, 2, 3, 4, 6, 8 h). After 8 h, the reactions were worked up. |
- 52
-
[ 17640-21-0 ]
-
[ 37143-54-7 ]
-
(R)-2-methoxy-N-(1-methoxypropan-2-yl)acetamide
[ No CAS ]
-
(1S)-2-methoxy-1-methylethylamine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
30% |
With lipase B from Candida antarctica immobilized on acrylic beads In toluene at 30℃; for 8h; Resolution of racemate; Enzymatic reaction; enantioselective reaction; |
4.4. Kinetic resolution of racemic amines rac-1a-i in shake flask
General procedure: Into a screw cap reaction vial were added a mixture of dry toluene (1.0 mL), immobilized CaLB enzyme (15.0 mg, CaLB-CV-T2-150), the corresponding racemic amine rac-1a-d (0.778 mmol) and the corresponding isopropyl 2-alkoxyacetate 2A-D (1.0 equiv., 0.778 mmol). The reaction mixture was shaken (750 rpm) at 30 °C and monitored by taking samples (20 mL) after different reaction times (0.25, 0.5, 1, 2, 3, 4, 6, 8 h). After 8 h, the reactions were worked up. |
- 53
-
1-amino-2,3-dihydro-1H-indene-4-carbonitrile
[ No CAS ]
-
[ 17640-21-0 ]
-
[ 1213099-69-4 ]
-
C13H14N2O2
[ No CAS ]
-
C13H14N2O2
[ No CAS ]
- 54
-
[ 17640-21-0 ]
-
[ 34698-41-4 ]
-
N-[(1R)-2,3-dihydro-1H-inden-1-yl]-2-methoxyacetamide
[ No CAS ]
-
(S)-1-Aminoindane
[ No CAS ]
-
[ 1213099-69-4 ]