Name: 54608-35-4|Ethyl 2-[(2-phenylethyl)amino]acetate|95%
Brand: Ambeed
SKU: A1129431
Rating: 95 (22 reviews)

1
[ 54608-35-4 ]
[ 7738-38-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In methanol at 20℃;
	With hydrogenchloride

Reference： [1]Weber, Dirk; Berger, Claudia; Eickelmann, Peter; Antel, Jochen; Kessler, Horst [Journal of Medicinal Chemistry, 2003, vol. 46, # 10, p. 1918 - 1930]
[2]Current Patent Assignee: RIEDEL J D - DE423027, 1925, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 15, p. 1711][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 15, p. 1711]

2
[ 105-36-2 ]
[ 64-04-0 ]
[ 54608-35-4 ]

Yield	Reaction Conditions	Operation in experiment
97%	With triethylamine In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;
93%	With triethylamine In dichloromethane for 2h;
90%	Stage #1: 2-phenyl-1-ethylamine With triethylamine In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: bromoacetic acid ethyl ester In dichloromethane at 20℃; Inert atmosphere;	4.1.1. Synthesis of 2-(phenethylamino)acetate (14a-f) General procedure: A solution of appropriate phenethylamine (2.99mmol, 1eq) in DCM (30mL) was cooled to 0°C before dropping wise addition of TEA (0.45mL, 4.49mmol, 1.5eq). After stirring under N2 atmosphere for 10min, the resulting mixture was treated drop wise with a solution of ethyl bromacetate (0.37mL, 3.29mmol, 1.1eq) in DCM (20mL). The cooling bath was removed, and the mixture was stirred overnight at rt then H2O (50mL) was added with vigorous stirring for 5min. The organic layer was separated, washed with brine, dried over Na2SO4, and concentrated under reduced pressure to give crude product which was purified by flash chromatography on silica gel using a mixture of EtOAc, hexanes (1:1) then pure EtOAc as eluent to yield desired product as a pale yellow oil. 4.1.1.1 Ethyl 2-(phenethylamino)acetate (14a) Yield % 90, pale yellow oil. 1H NMR (400MHz, δ ppm CDCl3): 7.35-7.11 (m, 5H, Ar-H), 4.09 (q, J=7.1Hz, 2H, OCH2CH3), 3.83 (s, 2H, CH2C=O), 2.78 (t, J=7.1Hz, 2H, NHCH2CH2), 2.55 (t, J=6.8Hz, 2H, NHCH2CH2), 1.20 (t, J=7.1Hz, 3H, OCH2CH3). 13C NMR (100MHz, δ ppm CDCl3): 169.5, 140.4, 128.5, 126.7, 125.0, 61.0, 50.9, 47.9, 35.3, 14.1. HRESI-MS m/z calcd for [M+H]+ C12H18NO2: 208.1332, found: 208.1330.

64%	With triethylamine In toluene at 20℃;
37%	With triethylamine In N,N-dimethyl-formamide	14 Preparation 14 Preparation 14 To a solution of 2-phenylethylamine (3.0 g, 24.8 mmol) in DMF (30 ml) was added ethyl bromoacetate (3.0 ml, 27.3 mmol) at 5° C. Then triethylamine (4.15 ml, 29.8 mmol) was added thereto at the same temperature. After stirring the resulting mixture at room temperature for 18 hours, the reaction mixture was diluted with EtOAc, washed with water and brine successively, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (methylene chloride:MeOH, 20:1) to give ethyl phenethylaminoacetate (1.87 g, 37%) as an oil. IR (neat, cm-1): 3028, 2935, 1738, 1454, 1201, 1146, 1028 1H-NMR (CDCl3, δ): 1.26 (3H, t, J=7.1 Hz), 2.74-2.94 (4H, m), 3.41 (2H,s), 4.17 (2H, q, J=7.1 Hz), 7.15-7.35 (5H, m) MS (m/z): 208 (M+H+)
3.6%	With pyridine; diethylamine at 20℃; for 24h;	3.4.4. Ethyl 2-(phenethylamino)acetate (6) 2-Phenethylamine (6 mmol, 755 μL) was dissolved in pyridine (500 μL) and a mixture of ethyl bromoacetate (6 mmol, 660 μL) and diethylamine (0.6 mmol, 60 μL) was added to the solution. The resulting mixture was stirred for 24 h at room temperature. The products were purified by silica gel flash column chromatography (acetone) and then reversed-phase HPLC (Capcell pak C18 AQ, 50% MeOH) to obtain 6 (45.4 mg, 3.6% yield). Compound 6: 1H NMR (CDCl3, 270 MHz) δ 7.12-7.29 (5H, m), δ 4.14 (2H, q, 7.0), δ 3.31 (2H, s), δ 2.87 (2H, t, 2.7), δ 2.77 (2H, t, 2.7), δ 1.23 (3H, t, 7.0); ESIMS m/z 208 [M+H]+; HRESIMS m/z 208.1338 [M+H]+ (calcd for C12H19N1O2, 208.1359).
	In diethyl ether
	In chloroform at 20℃; for 2h;
	In chloroform for 2h;
	In chloroform at 20℃; for 2h;
	With triethylamine In dichloromethane at 0 - 20℃;

Reference： [1]Einsiedel, Jürgen; Held, Cornelia; Hervet, Maud; Plomer, Manuel; Tschammer, Nuska; Hübner, Harald; Gmeiner, Peter [Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 2915 - 2923]
[2]Kwon, Oh-Seok; Ahn, Sungjin; Jeon, Ju-Eun; Park, In Guk; Won, Tae Hyung; Sim, Chung J.; Park, Hyeung-Geun; Oh, Dong-Chan; Oh, Ki-Bong; Noh, Minsoo; Shin, Jongheon [Organic Letters, 2021, vol. 23, # 12, p. 4667 - 4671]
[3]Abdelrahman, Mostafa H.; Abdu-Allah, Hajjaj H. M.; Abou-Ghadir, Ola F.; Al-Wahaibi, Lamya H.; Ali, Asmaa T.; Farghaly, Hatem S.; Gouda, Ahmed M.; Salem, Ola I. A.; Trembleau, Laurent; Youssif, Bahaa G. M. [Bioorganic Chemistry, 2020, vol. 104]
[4]Weber, Dirk; Berger, Claudia; Eickelmann, Peter; Antel, Jochen; Kessler, Horst [Journal of Medicinal Chemistry, 2003, vol. 46, # 10, p. 1918 - 1930]
[5]Current Patent Assignee: ASTELLAS PHARMA INC. - US6437146, 2002, B1
[6]Location in patent: experimental part Choi, Jae-Hoon; Ozawa, Nobuhiko; Yamakawa, Yasuhiro; Nagai, Kaoru; Hirai, Hirofumi; Kawagishi, Hirokazu [Tetrahedron, 2011, vol. 67, # 35, p. 6649 - 6653]
[7]KIER; DHAWAN [Journal of Pharmaceutical Sciences, 1962, vol. 51, p. 1058 - 1061]
[8]Carmi, Caterina; Cavazzoni, Andrea; Zuliani, Valentina; Lodola, Alessio; Bordi, Fabrizio; Plazzi, Pier Vincenzo; Alfieri, Roberta R.; Petronini, Pier Giorgio; Mor, Marco [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 15, p. 4021 - 4025]
[9]Location in patent: experimental part Zuliani, Valentina; Carmi, Caterina; Rivara, Mirko; Fantini, Marco; Lodola, Alessio; Vacondio, Federica; Bordi, Fabrizio; Plazzi, Pier Vincenzo; Cavazzoni, Andrea; Galetti, Maricla; Alfieri, Roberta R.; Petronini, Pier Giorgio; Mor, Marco [European Journal of Medicinal Chemistry, 2009, vol. 44, # 9, p. 3471 - 3479]
[10]Jadhav, Gopal P.; Kaur, Ishwinder; Maryati, Maryati; Airhihen, Blessing; Fischer, Peter M.; Winkler, G. Sebastiaan [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 19, p. 4219 - 4224]
[11]Current Patent Assignee: RIEDEL J D - DE423027, 1925, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 15, p. 1711][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 15, p. 1711]
[12]Abdelrahman, Mostafa H.; Ali, Asmaa T.; Alzarea, Sami I.; Gomaa, Hesham A. M.; Gouda, Ahmed M.; Hendawy, O. M.; Mohamed, Fatma A. M.; Morcoss, Martha M.; Shaker, Mohamed E.; Trembleau, Laurent; Youssif, Bahaa G. M. [Bioorganic Chemistry, 2022, vol. 120]

3
[ 54608-35-4 ]
[ 130406-42-7 ]
N-<N-<(2-adamantyloxy)carbonyl>-DL-α-methyltryptophanyl>-N-(2-phenylethyl)glycin ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine 1.) DMF, RT, 45 min, 2.) DMF, RT, 7 d; Yield given. Multistep reaction;

Reference： [1]Blommaert, Armand G.S.; Weng Jian-Hui; Dorville, Agnes; McCort, Isabelle; Ducos, Bertrand; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2868 - 2877]

4
[ 54608-35-4 ]
Boc-Arg(NO₂^G)-OIBC [ No CAS ]
C₂₃H₃₆N₆O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran 1.) -20 deg C, 10 min, 2.) RT, 1 h;

Reference： [1]Kikumoto; Tamao; Ohkubo; Tezuka; Tonomura; Okamoto; Hijikata [Journal of medicinal chemistry, 1980, vol. 23, # 12, p. 1293 - 1299]

5
[ 54608-35-4 ]
N-<(2-adamantyloxy)carbonyl>-D-tryptophan [ No CAS ]
N-<N-<(2-adamantyloxy)carbonyl>-D-tryptophanyl>-N-(2-phenylethyl)glycine ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine 1.) DMF, RT, 45 min, 2.) DMF, RT, 7 d; Yield given. Multistep reaction;

Reference： [1]Blommaert, Armand G.S.; Weng Jian-Hui; Dorville, Agnes; McCort, Isabelle; Ducos, Bertrand; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2868 - 2877]

6
[ 54608-35-4 ]
[ 1027023-64-8 ]
[ 1027093-01-1 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide for 72h; Ambient temperature;

Reference： [1]Blommaert, Armand G.S.; Weng Jian-Hui; Dorville, Agnes; McCort, Isabelle; Ducos, Bertrand; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2868 - 2877]

7
[ 54608-35-4 ]
[ 150871-34-4 ]
[2-(Adamantan-2-yloxycarbonylamino)-2-methyl-3-naphthalen-1-yl-propionyl]-phenethyl-amino}-acetic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	In N,N-dimethyl-formamide for 72h; Ambient temperature;

Reference： [1]Blommaert, Armand G.S.; Weng Jian-Hui; Dorville, Agnes; McCort, Isabelle; Ducos, Bertrand; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2868 - 2877]

8
[ 623-73-4 ]
[ 64-04-0 ]
[ 54608-35-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	In benzene for 48h; Ambient temperature;

Reference： [1]Zhu, Zuolin; Espenson, James H. [Journal of the American Chemical Society, 1996, vol. 118, # 41, p. 9901 - 9907]

9
[ 26607-51-2 ]
[ 54608-35-4 ]
[((R)-2-Benzyloxycarbonylamino-propionyl)-phenethyl-amino]-acetic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 24h;
	With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 24h;

Reference： [1]Sanchez; Ramos; Avendano [Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5731 - 5735]
[2]Sanchez; Ramos; Avendano [Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5731 - 5735]

10
[ 1142-20-7 ]
[ 54608-35-4 ]
[((S)-2-Benzyloxycarbonylamino-propionyl)-phenethyl-amino]-acetic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 24h;
	With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 24h;

Reference： [1]Sanchez; Ramos; Avendano [Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5731 - 5735]
[2]Sanchez; Ramos; Avendano [Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5731 - 5735]

11
[ 4530-20-5 ]
[ 54608-35-4 ]
[ 856702-35-7 ]

Yield	Reaction Conditions	Operation in experiment
0.702 g	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;

Reference： [1]Lopez-Cobenas, Alberto; Cledera, Pilar; Sanchez, J. Domingo; Lopez-Alvarado, Pilar; Ramos, M. Teresa; Avendano, Carmen; Menendez, J. Carlos [Synthesis, 2005, # 19, p. 3412 - 3422]

12
[ 13734-41-3 ]
[ 54608-35-4 ]
[ 856702-32-4 ]

Yield	Reaction Conditions	Operation in experiment
0.74 g	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;

Reference： [1]Lopez-Cobenas, Alberto; Cledera, Pilar; Sanchez, J. Domingo; Lopez-Alvarado, Pilar; Ramos, M. Teresa; Avendano, Carmen; Menendez, J. Carlos [Synthesis, 2005, # 19, p. 3412 - 3422]

13
[ 623-33-6 ]
[ 122-78-1 ]
[ 54608-35-4 ]

Yield	Reaction Conditions	Operation in experiment
49%	With sodium cyanoborohydride In ethanol at 20℃; for 24h;

Reference： [1]Lopez-Cobenas, Alberto; Cledera, Pilar; Sanchez, J. Domingo; Lopez-Alvarado, Pilar; Ramos, M. Teresa; Avendano, Carmen; Menendez, J. Carlos [Synthesis, 2005, # 19, p. 3412 - 3422]

14
[ 623-33-6 ]
[ 64-04-0 ]
[ 54608-35-4 ]
[ 3272-80-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 45% 2: 15%	In ethanol for 24h;

Reference： [1]Lopez-Cobenas, Alberto; Cledera, Pilar; Sanchez, J. Domingo; Lopez-Alvarado, Pilar; Ramos, M. Teresa; Avendano, Carmen; Menendez, J. Carlos [Synthesis, 2005, # 19, p. 3412 - 3422]

15
[ 590-28-3 ]
[ 54608-35-4 ]
[ 54608-34-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	With hydrogenchloride In water at 20℃; Cooling with ice;
	With water at 20℃; for 20h;

Reference： [1]Location in patent: experimental part Zuliani, Valentina; Carmi, Caterina; Rivara, Mirko; Fantini, Marco; Lodola, Alessio; Vacondio, Federica; Bordi, Fabrizio; Plazzi, Pier Vincenzo; Cavazzoni, Andrea; Galetti, Maricla; Alfieri, Roberta R.; Petronini, Pier Giorgio; Mor, Marco [European Journal of Medicinal Chemistry, 2009, vol. 44, # 9, p. 3471 - 3479]
[2]Carmi, Caterina; Cavazzoni, Andrea; Zuliani, Valentina; Lodola, Alessio; Bordi, Fabrizio; Plazzi, Pier Vincenzo; Alfieri, Roberta R.; Petronini, Pier Giorgio; Mor, Marco [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 15, p. 4021 - 4025]

16
[ 54608-35-4 ]
1-(2-phenylethyl)-2,5-piperazinedione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 0.702 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide*HCl / CH₂Cl₂ / 24 h / 20 °C 2: 99 percent / 0.05 h / microwave irradiation

Reference： [1]Lopez-Cobenas, Alberto; Cledera, Pilar; Sanchez, J. Domingo; Lopez-Alvarado, Pilar; Ramos, M. Teresa; Avendano, Carmen; Menendez, J. Carlos [Synthesis, 2005, # 19, p. 3412 - 3422]

17
[ 54608-35-4 ]
[ 856702-36-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 0.74 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide*HCl / CH₂Cl₂ / 24 h / 20 °C 2: 90 percent / 0.05 h / microwave irradiation

Reference： [1]Lopez-Cobenas, Alberto; Cledera, Pilar; Sanchez, J. Domingo; Lopez-Alvarado, Pilar; Ramos, M. Teresa; Avendano, Carmen; Menendez, J. Carlos [Synthesis, 2005, # 19, p. 3412 - 3422]

18
[ 54608-35-4 ]
[((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-phenethyl-amino]-acetic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: EDC / CH₂Cl₂ / 24 h / 20 °C 2: EDC / CH₂Cl₂ / 24 h / 20 °C

Reference： [1]Sanchez; Ramos; Avendano [Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5731 - 5735]

19
[ 54608-35-4 ]
N-<N-<(2-adamantyloxy)carbonyl>-DL-α-methyl-3-(2-phenylethyl)alaninyl>-N-(2-phenylethyl)glycine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dimethylformamide / 72 h / Ambient temperature 2: aq. LiOH / ethanol; dioxane / Ambient temperature

Reference： [1]Blommaert, Armand G.S.; Weng Jian-Hui; Dorville, Agnes; McCort, Isabelle; Ducos, Bertrand; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2868 - 2877]

20
[ 54608-35-4 ]
N-<N-<(2-adamantyloxy)carbonyl>-D-tryptophanyl>-N-(2-phenylethyl)glycine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) BOP, DIEA / 1.) DMF, RT, 45 min, 2.) DMF, RT, 7 d 2: 88 percent / aq. LiOH / dioxane; ethanol / Ambient temperature

Reference： [1]Blommaert, Armand G.S.; Weng Jian-Hui; Dorville, Agnes; McCort, Isabelle; Ducos, Bertrand; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2868 - 2877]

21
[ 54608-35-4 ]
N-<N-<(2-adamantyloxy)carbonyl>-DL-α-methyl-3-(4-bromophenyl)alaninyl>-N-(2-phenylethyl)glycine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dimethylformamide / 72 h / Ambient temperature 2: aq. LiOH / ethanol; dioxane / Ambient temperature

Reference： [1]Blommaert, Armand G.S.; Weng Jian-Hui; Dorville, Agnes; McCort, Isabelle; Ducos, Bertrand; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2868 - 2877]

22
[ 54608-35-4 ]
N-<N-<(2-adamantyloxy)carbonyl>-DL-α-methyl-3-(1-naphthyl)alaninyl>-N-(2-phenylethyl)glycine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 84 percent / dimethylformamide / 72 h / Ambient temperature 2: 53 percent / aq. LiOH / ethanol; dioxane / Ambient temperature

Reference： [1]Blommaert, Armand G.S.; Weng Jian-Hui; Dorville, Agnes; McCort, Isabelle; Ducos, Bertrand; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2868 - 2877]

23
[ 54608-35-4 ]
N-<N-<(2-adamantyloxy)carbonyl>-DL-α-methyl-3-(2-naphthyl)alaninyl>-N-(2-phenylethyl)glycine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dimethylformamide / 72 h / Ambient temperature 2: aq. LiOH / ethanol; dioxane / Ambient temperature

Reference： [1]Blommaert, Armand G.S.; Weng Jian-Hui; Dorville, Agnes; McCort, Isabelle; Ducos, Bertrand; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2868 - 2877]

24
[ 54608-35-4 ]
PD 141949 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) BOP, DIEA / 1.) DMF, RT, 45 min, 2.) DMF, RT, 7 d 2: 93 percent / aq. LiOH / dioxane; ethanol / Ambient temperature

Reference： [1]Blommaert, Armand G.S.; Weng Jian-Hui; Dorville, Agnes; McCort, Isabelle; Ducos, Bertrand; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2868 - 2877]

25
[ 54608-35-4 ]
[ 63921-70-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: tetrahydrofuran / 1.) -20 deg C, 10 min, 2.) RT, 1 h 2: HCl / ethyl acetate / 3 h 3: Et₃N / CH₂Cl₂ / 4 h 4: H₂ / Pd black / ethanol; acetic acid / 30 h / Ambient temperature 5: 1 N aq. NaOH / ethanol / 30 h / Ambient temperature

Reference： [1]Kikumoto; Tamao; Ohkubo; Tezuka; Tonomura; Okamoto; Hijikata [Journal of medicinal chemistry, 1980, vol. 23, # 12, p. 1293 - 1299]

26
[ 54608-35-4 ]
[(S)-2-(6,7-Dimethoxy-naphthalene-2-sulfonylamino)-5-guanidino-pentanoyl]-phenethyl-amino}-acetic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: tetrahydrofuran / 1.) -20 deg C, 10 min, 2.) RT, 1 h 2: HCl / ethyl acetate / 3 h 3: Et₃N / CH₂Cl₂ / 4 h 4: H₂ / Pd black / ethanol; acetic acid / 30 h / Ambient temperature

Reference： [1]Kikumoto; Tamao; Ohkubo; Tezuka; Tonomura; Okamoto; Hijikata [Journal of medicinal chemistry, 1980, vol. 23, # 12, p. 1293 - 1299]

27
[ 54608-35-4 ]
C₁₈H₂₈N₆O₅*ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 1.) -20 deg C, 10 min, 2.) RT, 1 h 2: HCl / ethyl acetate / 3 h

Reference： [1]Kikumoto; Tamao; Ohkubo; Tezuka; Tonomura; Okamoto; Hijikata [Journal of medicinal chemistry, 1980, vol. 23, # 12, p. 1293 - 1299]

28
[ 54608-35-4 ]
C₃₀H₃₈N₆O₉S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrahydrofuran / 1.) -20 deg C, 10 min, 2.) RT, 1 h 2: HCl / ethyl acetate / 3 h 3: Et₃N / CH₂Cl₂ / 4 h

Reference： [1]Kikumoto; Tamao; Ohkubo; Tezuka; Tonomura; Okamoto; Hijikata [Journal of medicinal chemistry, 1980, vol. 23, # 12, p. 1293 - 1299]

29
[ 54608-35-4 ]
[ 179179-43-2 ]

Yield	Reaction Conditions	Operation in experiment
76%		6.i Example 6 i) The procedure of Example 5-i) was repeated replacing the glycine ester with N-phenethylglycine ethyl ester (414 mg, 2 mmol) and the resultant product was recrystallized from ethyl acetate-hexane to give N-[3-(4,5,7-trifluorobenzothiazol-2-yl)propionyl]-N-phenethylglycine ethyl ester (680 mg, 76%) as a colorless powder. m.p.78° to 81° C. NMR(CDCl3) δ:1.25 (1.27) (3H,t,J=7.2 Hz), 2.78-2.98 (4H,m), 3.39 (3.50) (2H,t,J=6.9 Hz), 3.65 (3.62) (2H,t,J=6.9 Hz), 4.02 (3.93) (2H,s), 4.17 (4.20) (2H,q,J=7.2 Hz), 6.95-7.05 (1H,m), 7.15-7.35 (5H,m)

Reference： [1]Current Patent Assignee: ASKA PHARMACEUTICAL CO., LTD. - US5700819, 1997, A

30
[ 924-44-7 ]
[ 64-04-0 ]
[ 54608-35-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: glyoxylic acid ethyl ester; phenethylamine In ethanol; toluene at 20℃; for 1h; Stage #2: With sodium cyanoborohydride; acetic acid In ethanol; toluene for 2h; Stage #3: With sodium chloride; sodium hydroxide

Reference： [1]Location in patent: experimental part Messeguer, Joaquim; Masip, Isabel; Montolio, Marisol; del Rio, Jose Antonio; Soriano, Eduardo; Messeguer, Angel [Tetrahedron, 2010, vol. 66, # 13, p. 2444 - 2454]

31
[ 54608-35-4 ]
[ 2937-50-0 ]
[ 1223389-60-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate In dichloromethane at 5℃;

Reference： [1]Location in patent: experimental part Messeguer, Joaquim; Masip, Isabel; Montolio, Marisol; del Rio, Jose Antonio; Soriano, Eduardo; Messeguer, Angel [Tetrahedron, 2010, vol. 66, # 13, p. 2444 - 2454]

32
[ 54608-35-4 ]
[ 82911-69-1 ]
2-{1-(2-phenylethyl)-[(9H-fluoren-9-ylmethoxy)carbonyl]amino}acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: N-phenethylglycine ethyl ester With sodium hydroxide In methanol for 0.5h; Inert atmosphere; Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide With hydrogenchloride In 1,4-dioxane; water at 0 - 20℃; Inert atmosphere;

Reference： [1]Einsiedel, Jürgen; Held, Cornelia; Hervet, Maud; Plomer, Manuel; Tschammer, Nuska; Hübner, Harald; Gmeiner, Peter [Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 2915 - 2923]

33
[ 64-18-6 ]
[ 54608-35-4 ]
[ 1332713-38-8 ]

Yield	Reaction Conditions	Operation in experiment
33%	With pyridine; diisopropyl-carbodiimide at 20℃; for 24h;	3.4.8. Ethyl 2-(N-phenethylformamido)acetate (1) Compound 6 (100 mmol, 20 mg) was dissolved in pyridine (500 μL) and a mixture of formic acid (0.4 mmol, 15 μL) and DIPCD (0.4 mmol, 60 μL) was added to the solution. The resulting mixture was stirred for 24 h at room temperature. The products were purified by silica gel flash column chromatography (CH2Cl2; CH2Cl2/acetone 9:1, 5:5; acetone; acetone/MeOH 5:5) and then reverse-phase HPLC (Capcell pak C18 AQ, 50% MeOH) to give 1 (7.7 mg, 33%);

Reference： [1]Location in patent: experimental part Choi, Jae-Hoon; Ozawa, Nobuhiko; Yamakawa, Yasuhiro; Nagai, Kaoru; Hirai, Hirofumi; Kawagishi, Hirokazu [Tetrahedron, 2011, vol. 67, # 35, p. 6649 - 6653]

34
[ 54608-35-4 ]
[ 75-36-5 ]
[ 1332457-48-3 ]

Yield	Reaction Conditions	Operation in experiment
19%	With pyridine; diisopropyl-carbodiimide at 20℃; for 24h;	3.4.5. Ethyl 2-(N-phenethylacetamido)acetate (7) Compound 6 (100 mmol, 20 mg) was dissolved in pyridine (500 μL) and a mixture of acetyl chloride (0.4 mmol, 30 μL) and DIPCD (0.4 mmol, 60 μL) was added to the solution. The resulting mixture was stirred for 24 h at room temperature. The products were purified by silica gel flash column chromatography (CH2Cl2; CH2Cl2/acetone 9:1, 5:5; acetone; acetone/MeOH 5:5) and then reversed-phase HPLC (Capcell pak C18 AQ, 50% MeOH) to give 7 (4.7 mg, 19% yield). Compound 7 was obtained a set of rotational isomers (7a and 7b). The molar ratio of 7a to 7b was 2.5 to 1. Compound 7a: 1H NMR (CD3OD, 270 MHz) δ 7.19-7.32 (5H, m, H-2, H-3, H-4, H-5, H-6), δ 4.18 (2H, q, 7.0, H-1'), δ 4.04 (2H, s, H-2), δ 3.63 (2H, t, 7.2, H-1'), δ 2.88 (2H, t, 7.1, H-2'), δ 1.86 (3H, s, NCO-Me), δ 1.26 (3H, t, 7.0, H-2'). 7b: δ 7.19-7.32 (5H, m, H-2, H-3, H-4, H-5, H-6), δ 4.18 (2H, q, 7.0, H-1'), δ 4.09 (2H, s, H-2), δ 3.55 (2H, t, 7.7, H-1'), δ 2.80 (2H, t, 7.6, H-2'), δ 2.01 (3H, s, NCO-Me), δ 1.26 (3H, t, 7.0, H-2'); ESIMS m/z 272 [M+Na]+; HRESIMS m/z 272.1254 [M+Na]+ (calcd for C14H19N1NaO3, 272.1262).

Reference： [1]Location in patent: experimental part Choi, Jae-Hoon; Ozawa, Nobuhiko; Yamakawa, Yasuhiro; Nagai, Kaoru; Hirai, Hirofumi; Kawagishi, Hirokazu [Tetrahedron, 2011, vol. 67, # 35, p. 6649 - 6653]

35
[ 54608-35-4 ]
[ 106-95-6 ]
[ 1375092-49-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 48h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Nemoto, Hisao; Tamagawa, Shin-Ya; Yatsuzuka, Kenji; Kawamura, Tomoyuki [Journal of Organic Chemistry, 2012, vol. 77, # 10, p. 4696 - 4705]

36
[ 623-33-6 ]
[ 103-63-9 ]
[ 54608-35-4 ]

Yield	Reaction Conditions	Operation in experiment
46%	With potassium carbonate; potassium iodide In acetonitrile for 24h; Reflux; Inert atmosphere;
37%	With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 48h;	9-1 Preparation Example 9-1) Preparation of phenethylamino-acetic acid ethyl ester (2-bromoethyl)benzene (1 g, 5.40 mmol), glycine ethyl ester hydrochloride (1.130 g, 8.11 mmol), and diisopropylethylamine (2.83 mL, 16.2 mmol) were dissolved in acetonitrile (20 mL). The mixture was stirred for 48 hours at room temperature under nitrogen atmosphere. The reaction solution was concentrated under reduced pressure, added to a saturated aqueous sodium hydrogen carbonate solution (30 mL), extracted with ethyl acetate (30 mL x 2), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the title compound (0.41 g, 37%) was obtained as a yellow solid.

Reference： [1]Location in patent: experimental part Nemoto, Hisao; Tamagawa, Shin-Ya; Yatsuzuka, Kenji; Kawamura, Tomoyuki [Journal of Organic Chemistry, 2012, vol. 77, # 10, p. 4696 - 4705]
[2]Current Patent Assignee: LEGOCHEM BIOSCIENCES INC. - KR2015/136294, 2015, A Location in patent: Paragraph 0203-0207

37
[ 623-73-4 ]
[ 54608-35-4 ]
diethyl 1-phenethyl-1H-1,2,3-triazole-4,5-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With oxygen; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(ll) bromide In N,N-dimethyl-formamide at 20℃; for 10h;

Reference： [1]Li, Yi-Jin; Li, Xue; Zhang, Shao-Xiao; Zhao, Yu-Long; Liu, Qun [Chemical Communications, 2015, vol. 51, # 58, p. 11564 - 11567]

38
[ 103-63-9 ]
[ 459-73-4 ]
[ 54608-35-4 ]

Yield	Reaction Conditions	Operation in experiment
37%	With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 48h;	Procedure for Synthesis of Benzyl-(2-hydroxyiminoethyl)-Carbamic Acid tert-Butyl Ester/(2-hydroxyiminoethyl)-phenethyl-Carbamic Acid tert-Butyl Ester (Scheme 6). General procedure: (2-Bromoethyl)benzene, 17 (1 g, 5.40 mmol),ethyl glycinate (130 g, 8.11 mmol), and DIPEA (2.83 mL,16.2 mmol) were dissolved in ACN, stirred for 48 h, and extracted with ethyl acetate (30 mL × 2) to yield compounds 18 (1.41 g, 37%). Compounds 18 in 1,4-dioxane (20 mL) were mixed with Na2CO3 (1.08 g, 10.2 mmol)and Boc2O (1.78 g, 8.16 mmol), stirred for 5 h, and extracted with ammonium chloride (100 mL) and ethyl acetate (50 mL) to give 19. The products were dissolved in THF (30 mL), cooled to -20C, lithium aluminum hydride (8.84 mL, 8.84 mmol) was added slowly, and this mixture was stirred for 1 h to give 20 (2.43 g, 99%) through column chromatography. The products were dried and then dissolved in DCM/DMSO (20 mL). The reaction mixture was cooled to 0C and stirred for 3 h after adding the SO3 pyridine complex (2.94 g, 18.3 mmol) and TEA(5.15 mL, 36.6 mmol). The mixture was extracted with 1 N HCl solution (30 mL) and ethyl acetate (50 mL × 2)to yield 21. These products were dissolved in ethanol (30 mL), NH2OHHCl salt and NaCO3 were added, and the mixture was stirred for 8 h. The reaction mixture was extracted with ethyl acetate (50 mL) and distilled water(50 mL) to yield 22 (2.17 g, 76%). Compound 18: 1HNMR(600 MHz, CDCl3) δ 7.30-7.19 (m, 5 H), 4.16 (q,J = 7.2 Hz, 2 H), 3.39 (s, 2 H ), 2.89 (t, J = 2.7 Hz, 2 H),2.81 (t, J = 12.4 Hz, 2 H), 1.25 (t, J = 7.2 Hz, 3 H). Compound19: 1H-NMR (600 MHz, CDCl3) δ 7.29-7.15 (m,5 H), 4.16 (q, J = 14.4 Hz, 2 H), 3.70 (s, 2 H ), 2.82 (m,2 H), 1.47 (s, 9 H), 1.25 (t, J = 18 Hz, 3 H). Compound20: 1H-NMR (600 MHz, CDCl3) δ 7.30-7.17 (m, 5 H),3.70 (s, 2 H), 3.49 (s, 2 H ), 3.44 (s, 2 H), 2.87 (s, 2 H),1.29 (s, 9 H). Compound 21: 1H-NMR (600 MHz, CDCl3)δ 9.47 (S, 1 H), 7.30-7.14 (m, 5 H), 4.12 (s, 1 H), 3.82 (s,2 H ), 3.54-3.47 (m, 2 H), 2.87-2.80 (m, 2 H), 1.26 (s,9 H). Compound 22: 1H-NMR (600 MHz, CDCl3) δ 8.47(s, 1 H), 7.43-7.15 (m, 5 H), 3.91 (m, 2 H), 3.44 (m, 2 H), 2.82 (m, 2 H), 1.26 (s, 9 H).

Reference： [1]Lee, Myeong Hwi; Song, Ho Young; Kim, Hyoungrae; Park, Kyung Eun; Kim, Jinyeong; Park, Tae Kyo; Kim, Yong Ju; Kang, Nam Sook [Bulletin of the Korean Chemical Society, 2016, vol. 37, # 7, p. 1105 - 1113]

39
[ 54608-35-4 ]
[ 949902-88-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium carbonate / 1,4-dioxane / 5 h 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -20 °C
	Multi-step reaction with 2 steps 1: sodium carbonate / water; 1,4-dioxane / 5 h / 20 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere

Reference： [1]Lee, Myeong Hwi; Song, Ho Young; Kim, Hyoungrae; Park, Kyung Eun; Kim, Jinyeong; Park, Tae Kyo; Kim, Yong Ju; Kang, Nam Sook [Bulletin of the Korean Chemical Society, 2016, vol. 37, # 7, p. 1105 - 1113]
[2]Current Patent Assignee: LEGOCHEM BIOSCIENCES INC. - KR2015/136294, 2015, A

40
[ 54608-35-4 ]
[ 182921-00-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium carbonate / 1,4-dioxane / 5 h 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -20 °C 3: sulfur trioxide pyridine complex; triethylamine / dichloromethane; dimethyl sulfoxide / 3 h / 0 °C
	Multi-step reaction with 3 steps 1: sodium carbonate / water; 1,4-dioxane / 5 h / 20 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 3: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide; dichloromethane / 3 h / 0 °C

Reference： [1]Lee, Myeong Hwi; Song, Ho Young; Kim, Hyoungrae; Park, Kyung Eun; Kim, Jinyeong; Park, Tae Kyo; Kim, Yong Ju; Kang, Nam Sook [Bulletin of the Korean Chemical Society, 2016, vol. 37, # 7, p. 1105 - 1113]
[2]Current Patent Assignee: LEGOCHEM BIOSCIENCES INC. - KR2015/136294, 2015, A

41
[ 54608-35-4 ]
t-butyl 2-(hydroxyimino)ethyl(phenethyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: sodium carbonate / 1,4-dioxane / 5 h 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -20 °C 3: sulfur trioxide pyridine complex; triethylamine / dichloromethane; dimethyl sulfoxide / 3 h / 0 °C 4: hydroxylamine hydrochloride; sodium carbonate / ethanol / 8 h / 20 °C
	Multi-step reaction with 4 steps 1: sodium carbonate / water; 1,4-dioxane / 5 h / 20 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 3: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide; dichloromethane / 3 h / 0 °C 4: hydroxylamine hydrochloride; sodium carbonate / ethanol / 8 h / 20 °C / Inert atmosphere

Reference： [1]Lee, Myeong Hwi; Song, Ho Young; Kim, Hyoungrae; Park, Kyung Eun; Kim, Jinyeong; Park, Tae Kyo; Kim, Yong Ju; Kang, Nam Sook [Bulletin of the Korean Chemical Society, 2016, vol. 37, # 7, p. 1105 - 1113]
[2]Current Patent Assignee: LEGOCHEM BIOSCIENCES INC. - KR2015/136294, 2015, A

42
[ 54608-35-4 ]
[5-[5-chloro-2-tetrazol-1-yl-phenyl]isooxazol-3-yl-methyl]phenethylcarbamic acid t-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: sodium carbonate / 1,4-dioxane / 5 h 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -20 °C 3.1: sulfur trioxide pyridine complex; triethylamine / dichloromethane; dimethyl sulfoxide / 3 h / 0 °C 4.1: hydroxylamine hydrochloride; sodium carbonate / ethanol / 8 h / 20 °C 5.1: N-chloro-succinimide; triethylamine / N,N-dimethyl-formamide 5.2: 2 h / 0 °C
	Multi-step reaction with 5 steps 1.1: sodium carbonate / water; 1,4-dioxane / 5 h / 20 °C / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 3.1: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide; dichloromethane / 3 h / 0 °C 4.1: hydroxylamine hydrochloride; sodium carbonate / ethanol / 8 h / 20 °C / Inert atmosphere 5.1: N-chloro-succinimide / N,N-dimethyl-formamide / 2 h / 0 °C 5.2: 5 h / 0 - 20 °C

Reference： [1]Lee, Myeong Hwi; Song, Ho Young; Kim, Hyoungrae; Park, Kyung Eun; Kim, Jinyeong; Park, Tae Kyo; Kim, Yong Ju; Kang, Nam Sook [Bulletin of the Korean Chemical Society, 2016, vol. 37, # 7, p. 1105 - 1113]
[2]Current Patent Assignee: LEGOCHEM BIOSCIENCES INC. - KR2015/136294, 2015, A

43
[ 24424-99-5 ]
[ 54608-35-4 ]
[ 193818-10-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In 1,4-dioxane for 5h;	Procedure for Synthesis of Benzyl-(2-hydroxyiminoethyl)-Carbamic Acid tert-Butyl Ester/(2-hydroxyiminoethyl)-phenethyl-Carbamic Acid tert-Butyl Ester (Scheme 6). General procedure: (2-Bromoethyl)benzene, 17 (1 g, 5.40 mmol),ethyl glycinate (130 g, 8.11 mmol), and DIPEA (2.83 mL,16.2 mmol) were dissolved in ACN, stirred for 48 h, and extracted with ethyl acetate (30 mL × 2) to yield compounds 18 (1.41 g, 37%). Compounds 18 in 1,4-dioxane (20 mL) were mixed with Na2CO3 (1.08 g, 10.2 mmol)and Boc2O (1.78 g, 8.16 mmol), stirred for 5 h, and extracted with ammonium chloride (100 mL) and ethyl acetate (50 mL) to give 19. The products were dissolved in THF (30 mL), cooled to -20C, lithium aluminum hydride (8.84 mL, 8.84 mmol) was added slowly, and this mixture was stirred for 1 h to give 20 (2.43 g, 99%) through column chromatography. The products were dried and then dissolved in DCM/DMSO (20 mL). The reaction mixture was cooled to 0C and stirred for 3 h after adding the SO3 pyridine complex (2.94 g, 18.3 mmol) and TEA(5.15 mL, 36.6 mmol). The mixture was extracted with 1 N HCl solution (30 mL) and ethyl acetate (50 mL × 2)to yield 21. These products were dissolved in ethanol (30 mL), NH2OHHCl salt and NaCO3 were added, and the mixture was stirred for 8 h. The reaction mixture was extracted with ethyl acetate (50 mL) and distilled water(50 mL) to yield 22 (2.17 g, 76%). Compound 18: 1HNMR(600 MHz, CDCl3) δ 7.30-7.19 (m, 5 H), 4.16 (q,J = 7.2 Hz, 2 H), 3.39 (s, 2 H ), 2.89 (t, J = 2.7 Hz, 2 H),2.81 (t, J = 12.4 Hz, 2 H), 1.25 (t, J = 7.2 Hz, 3 H). Compound19: 1H-NMR (600 MHz, CDCl3) δ 7.29-7.15 (m,5 H), 4.16 (q, J = 14.4 Hz, 2 H), 3.70 (s, 2 H ), 2.82 (m,2 H), 1.47 (s, 9 H), 1.25 (t, J = 18 Hz, 3 H). Compound20: 1H-NMR (600 MHz, CDCl3) δ 7.30-7.17 (m, 5 H),3.70 (s, 2 H), 3.49 (s, 2 H ), 3.44 (s, 2 H), 2.87 (s, 2 H),1.29 (s, 9 H). Compound 21: 1H-NMR (600 MHz, CDCl3)δ 9.47 (S, 1 H), 7.30-7.14 (m, 5 H), 4.12 (s, 1 H), 3.82 (s,2 H ), 3.54-3.47 (m, 2 H), 2.87-2.80 (m, 2 H), 1.26 (s,9 H). Compound 22: 1H-NMR (600 MHz, CDCl3) δ 8.47(s, 1 H), 7.43-7.15 (m, 5 H), 3.91 (m, 2 H), 3.44 (m, 2 H), 2.82 (m, 2 H), 1.26 (s, 9 H).
	With sodium carbonate In 1,4-dioxane; water at 20℃; for 5h; Inert atmosphere;	9-2 Preparation Example 9-2) Preparation of (t-butoxycarbonyl-phenethyl-amino)-acetic acid ethyl ester After dissolving the compound (1.41 g, 6.80 mmol) obtained in Preparation Example 9-1 in 1,4-dioxane (20 mL) and distilled water (20 mL), sodium carbonate (1.08 g, 10.2 mmol) was added, followed by di-t- Butoxy dicarbonate (1.78 g, 8.16 mmol)After putting in, the mixture was stirred for 5 hours at room temperature under nitrogen atmosphere.The reaction solution was extracted with a saturated aqueous ammonium chloride solution (100 mL) and ethyl acetate (100 mL), and the organic layer was washed with an aqueous sodium chloride solution (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain a compound.

Reference： [1]Lee, Myeong Hwi; Song, Ho Young; Kim, Hyoungrae; Park, Kyung Eun; Kim, Jinyeong; Park, Tae Kyo; Kim, Yong Ju; Kang, Nam Sook [Bulletin of the Korean Chemical Society, 2016, vol. 37, # 7, p. 1105 - 1113]
[2]Current Patent Assignee: LEGOCHEM BIOSCIENCES INC. - KR2015/136294, 2015, A Location in patent: Paragraph 0203; 0204; 0208-0210

44
[ 10517-21-2 ]
[ 54608-35-4 ]
8-chloro-2-phenethyl-2,3-dihydropyrazino[1,2-a]indole-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%		General procedure: A mixture of appropriate indole-2-carboxylic acids 13a-g (0.63mmol, 1eq), BOP (0.36g, 0.82mmol, 1.3eq) and DIPEA (0.22mL, 1.26mmol, 2eq) in DCM (25mL) was stirred for 10min at rt before addition of appropriate phenethyl amino acetates 14a-f (0.76mmol, 1.2eq) and the resulting reaction mixture was stirred overnight at rt. After removing of the solvent in vacuo, the residue was extracted with EtOAc, washed with 5% HCl, saturated NaHCO3 solution, brine, dried over MgSO4, and evaporated under reduced pressure to give a crude product which was purified by flash chromatography on silica gel using EtOAc/hexanes (1:3) as eluent to give the corresponding dihydropyrazino-1,4-diones 15-33. 4.1.2.1 8-Chloro-2-phenethyl-2,3-dihydropyrazino[1,2-a]indole-1,4-dione (15) Yield % 82, mp 145-147C. 1H NMR (400MHz, δ ppm CDCl3): 8.30 (d, J=8.9Hz, 1H, Ar-H), 7.65 (d, J=2.1Hz, 1H, Ar-H), 7.43 (dd, J=8.8, 2.1Hz, 1H, Ar-H), 7.39-7.21 (m, 6H, Ar-H), 4.20 (s, 2H, CH2C=O), 3.83 (t, J=7.3Hz, 2H, NCH2CH2), 3.02 (t, J=7.9Hz, 2H, NCH2CH2). 13C NMR (100MHz, δ ppm CDCl3): 161.23 (CH2C=O), 155.48 (C=O), 137.96, 132.91, 131.10, 130.28, 129.84, 128.88, 128.69, 127.99, 126.93, 122.01, 117.39, 113.23, 52.54, 48.08, 33.41. HRESI-MS m/z calcd for [M+H]+ C19H16ClN2O2: 339.0895, found: 339.0895

Reference： [1]Bioorganic Chemistry,2020,vol. 104

45
[ 54608-35-4 ]
[ 16381-47-8 ]
8-chloro-10-methyl-2-phenethyl-2,3-dihydropyrazino[1,2-a]indole-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: 5-chloro-3-methyl-1H-indole-2-carboxylic acid With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.166667h; Stage #2: N-phenethylglycine ethyl ester In dichloromethane at 20℃;	4.1.2 Synthesis of compounds 15-33 General procedure: A mixture of appropriate indole-2-carboxylic acids 13a-g (0.63mmol, 1eq), BOP (0.36g, 0.82mmol, 1.3eq) and DIPEA (0.22mL, 1.26mmol, 2eq) in DCM (25mL) was stirred for 10min at rt before addition of appropriate phenethyl amino acetates 14a-f (0.76mmol, 1.2eq) and the resulting reaction mixture was stirred overnight at rt. After removing of the solvent in vacuo, the residue was extracted with EtOAc, washed with 5% HCl, saturated NaHCO3 solution, brine, dried over MgSO4, and evaporated under reduced pressure to give a crude product which was purified by flash chromatography on silica gel using EtOAc/hexanes (1:3) as eluent to give the corresponding dihydropyrazino-1,4-diones 15-33.

Reference： [1]Abdelrahman, Mostafa H.; Abdu-Allah, Hajjaj H. M.; Abou-Ghadir, Ola F.; Al-Wahaibi, Lamya H.; Ali, Asmaa T.; Farghaly, Hatem S.; Gouda, Ahmed M.; Salem, Ola I. A.; Trembleau, Laurent; Youssif, Bahaa G. M. [Bioorganic Chemistry, 2020, vol. 104]

46
[ 446830-67-7 ]
[ 54608-35-4 ]
8-chloro-10-ethyl-2-phenethyl-2,3-dihydropyrazino[1,2-a]indole-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: 5-chloro-3-ethyl-1H-indole-2-carboxylic acid With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.166667h; Stage #2: N-phenethylglycine ethyl ester In dichloromethane at 20℃;	4.1.2 Synthesis of compounds 15-33 General procedure: A mixture of appropriate indole-2-carboxylic acids 13a-g (0.63mmol, 1eq), BOP (0.36g, 0.82mmol, 1.3eq) and DIPEA (0.22mL, 1.26mmol, 2eq) in DCM (25mL) was stirred for 10min at rt before addition of appropriate phenethyl amino acetates 14a-f (0.76mmol, 1.2eq) and the resulting reaction mixture was stirred overnight at rt. After removing of the solvent in vacuo, the residue was extracted with EtOAc, washed with 5% HCl, saturated NaHCO3 solution, brine, dried over MgSO4, and evaporated under reduced pressure to give a crude product which was purified by flash chromatography on silica gel using EtOAc/hexanes (1:3) as eluent to give the corresponding dihydropyrazino-1,4-diones 15-33.

Reference： [1]Abdelrahman, Mostafa H.; Abdu-Allah, Hajjaj H. M.; Abou-Ghadir, Ola F.; Al-Wahaibi, Lamya H.; Ali, Asmaa T.; Farghaly, Hatem S.; Gouda, Ahmed M.; Salem, Ola I. A.; Trembleau, Laurent; Youssif, Bahaa G. M. [Bioorganic Chemistry, 2020, vol. 104]

47
[ 54608-35-4 ]
[ 79-03-8 ]
ethyl N-phenethyl-N-propionylglycinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine In chloroform at 0 - 25℃; for 1.83333h;

Reference： [1]Kwon, Oh-Seok; Ahn, Sungjin; Jeon, Ju-Eun; Park, In Guk; Won, Tae Hyung; Sim, Chung J.; Park, Hyeung-Geun; Oh, Dong-Chan; Oh, Ki-Bong; Noh, Minsoo; Shin, Jongheon [Organic Letters, 2021, vol. 23, # 12, p. 4667 - 4671]

48
[ 54608-35-4 ]
5-chloro-3-(ethoxymethyl)-1H-indole-2-carboxylic acid [ No CAS ]
8-chloro-10-(ethoxymethyl)-2-phenethyl-2,3-dihydro-pyrazino[1,2-a]indole-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: 5-chloro-3-(ethoxymethyl)-1H-indole-2-carboxylic acid With benzotriazole-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.166667h; Stage #2: N-phenethylglycine ethyl ester In dichloromethane at 20℃;	4.1.4 General procedure for synthesis of compounds 13-22 General procedure: A mixture of acids 4, 7, and 10 (0.74mmol, 1eq), BOP (0.42g, 0.95mmol, 1.25eq) and DIPEA (0.25mL, 1.50mmol, 2eq) in DCM (30mL) was stirred for 10min at rt, followed by addition of 12a-e (0.89mmol, 1.2eq). At rt, the resulting reaction mixture was stirred overnight. Following EtOAc extraction, the crude product was purified by flash chromatography using EtOAc/hexane (1:3) to yield the corresponding 13-22.

Reference： [1]Abdelrahman, Mostafa H.; Ali, Asmaa T.; Alzarea, Sami I.; Gomaa, Hesham A. M.; Gouda, Ahmed M.; Hendawy, O. M.; Mohamed, Fatma A. M.; Morcoss, Martha M.; Shaker, Mohamed E.; Trembleau, Laurent; Youssif, Bahaa G. M. [Bioorganic Chemistry, 2022, vol. 120]

49
[ 54608-35-4 ]
5-chloro-3-(hydroxymethyl)-1H-indole-2-carboxylic acid [ No CAS ]
8-chloro-10-(hydroxymethyl)-2-phenethyl-2,3-dihydropyrazino[1,2-a]indole-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: 5-chloro-3-(hydroxymethyl)-1H-indole-2-carboxylic acid With benzotriazole-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.166667h; Stage #2: N-phenethylglycine ethyl ester In dichloromethane at 20℃;	4.1.4 General procedure for synthesis of compounds 13-22 General procedure: A mixture of acids 4, 7, and 10 (0.74mmol, 1eq), BOP (0.42g, 0.95mmol, 1.25eq) and DIPEA (0.25mL, 1.50mmol, 2eq) in DCM (30mL) was stirred for 10min at rt, followed by addition of 12a-e (0.89mmol, 1.2eq). At rt, the resulting reaction mixture was stirred overnight. Following EtOAc extraction, the crude product was purified by flash chromatography using EtOAc/hexane (1:3) to yield the corresponding 13-22.

Reference： [1]Abdelrahman, Mostafa H.; Ali, Asmaa T.; Alzarea, Sami I.; Gomaa, Hesham A. M.; Gouda, Ahmed M.; Hendawy, O. M.; Mohamed, Fatma A. M.; Morcoss, Martha M.; Shaker, Mohamed E.; Trembleau, Laurent; Youssif, Bahaa G. M. [Bioorganic Chemistry, 2022, vol. 120]

50
[ 54608-35-4 ]
(E)-5-chloro-3-(2-methoxyvinyl)-1H-indole-2-carboxylic acid [ No CAS ]
(E)-8-chloro-10-(2-methoxyvinyl)-2-phenethyl-2,3-dihydropyrazino[1,2-a]indole-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: (E)-5-chloro-3-(2-methoxyvinyl)-1H-indole-2-carboxylic acid With benzotriazole-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.166667h; Stage #2: N-phenethylglycine ethyl ester In dichloromethane at 20℃;	4.1.4 General procedure for synthesis of compounds 13-22 General procedure: A mixture of acids 4, 7, and 10 (0.74mmol, 1eq), BOP (0.42g, 0.95mmol, 1.25eq) and DIPEA (0.25mL, 1.50mmol, 2eq) in DCM (30mL) was stirred for 10min at rt, followed by addition of 12a-e (0.89mmol, 1.2eq). At rt, the resulting reaction mixture was stirred overnight. Following EtOAc extraction, the crude product was purified by flash chromatography using EtOAc/hexane (1:3) to yield the corresponding 13-22.

Reference： [1]Abdelrahman, Mostafa H.; Ali, Asmaa T.; Alzarea, Sami I.; Gomaa, Hesham A. M.; Gouda, Ahmed M.; Hendawy, O. M.; Mohamed, Fatma A. M.; Morcoss, Martha M.; Shaker, Mohamed E.; Trembleau, Laurent; Youssif, Bahaa G. M. [Bioorganic Chemistry, 2022, vol. 120]

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	Inquiry	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ item.pr_usastock ]}		{[ item.pr_chinastock ]}	{[ item.pr_remark ]}

CAS No. :	54608-35-4	MDL No. :	MFCD11152837
Formula :	C₁₂H₁₇NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ADVKOLZYLWXQSH-UHFFFAOYSA-N
M.W :	207.27	Pubchem ID :	11031025
Synonyms :

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.42
Num. rotatable bonds :	7
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	59.53
TPSA :	38.33 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.12 cm/s

[ CAS No. 54608-35-4 ] {[proInfo.proName]}

Quality Control of [ 54608-35-4 ]

Related Doc. of [ 54608-35-4 ]

Product Details of [ 54608-35-4 ]

Calculated chemistry of [ 54608-35-4 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 54608-35-4 ]

Application In Synthesis of [ 54608-35-4 ]

[ 54608-35-4 ] Synthesis Path-Downstream 1~50

Technical Information

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Log Po/w (iLOGP) :	2.72
Log Po/w (XLOGP3) :	2.04
Log Po/w (WLOGP) :	1.38
Log Po/w (MLOGP) :	1.98
Log Po/w (SILICOS-IT) :	2.36
Consensus Log Po/w :	2.09

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Log S (ESOL) :	-2.24
Solubility :	1.18 mg/ml ; 0.0057 mol/l
Class :	Soluble
Log S (Ali) :	-2.47
Solubility :	0.697 mg/ml ; 0.00336 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.15
Solubility :	0.0146 mg/ml ; 0.0000706 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.52

Signal Word:	Danger	Class:	8
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P332+P313-P362-P403+P233-P405-P501	UN#:	1760
Hazard Statements:	H302-H315-H318-H335	Packing Group:	Ⅲ
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling