Name: 15028-39-4|(S)-Methyl 2-amino-2-phenylacetate hydrochloride|97%
Brand: Ambeed
SKU: A219969
Price: 6.0 USD
Availability: InStock
Rating: 99 (22 reviews)

1
[ 67-56-1 ]
[ 2935-35-5 ]
[ 15028-39-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With thionyl chloride for 10h; Ambient temperature;
97%	With thionyl chloride for 8h; Heating;
97%	With thionyl chloride In methanol at 20℃; Cooling with ice;

97.6%	With thionyl chloride at 0℃; for 2h;	2 Example 2 Amino-phenyl-acetic acid methyl ester hydrochloride salt (8). To a stirred solution of (S)-phenylglycine (50 g, 0.3 mol) in MeOH (500 mL) at 0° C. was added thionyl chloride (42.84 g, 0.36 mol) dropwise. After stirring for 2 h, the solvent was concentrated, and the precipitated solid was washed with diethyl ether to afford product 8 (65 g, 97.6%). 1H NMR (400 MHz, D2O) δ 3.70 (s, 3 H), 5.17 (s, 1 H), 7.35-7.41 (m, 5 H).
97.7%	With thionyl chloride at 0 - 75℃; for 2h;	First step General procedure: The methyl-esterification reaction of L-phenylalanine.To a suspension of L-phenylalanine (1 g, 6.05 mmol, 1.0 equiv) inmethanol (25 mL) cooled to 0 C was added thionyl chloride(475 mL, 6.66 mmol, 1.5 equiv) slowly. After 10 min, the reactionmixture was heated to 75 C to reflux for 2 h. After completion(monitored by TLC), the solvent was removed in vacuo, and at thistime, a white solid was formed methyl L-phenylalaninate hydrochloride(1.23 g, quantitative yield).
92%	With thionyl chloride for 0.333333h; Heating;
92%	With thionyl chloride at 0℃;
86%	With thionyl chloride at 0 - 75℃; for 6.5h;
85%	With hydrogenchloride for 30h; Ambient temperature;
78%	With thionyl chloride Heating;
	With thionyl chloride 1) RT, 30 min, 2) 40 deg C, 2 h; Yield given;
	With thionyl chloride at 40℃; for 3h;
	With thionyl chloride 2 h, room temperature; reflux;
1.3 g	With thionyl chloride for 48h; Ambient temperature;
	With thionyl chloride for 20h; Ambient temperature; Yield given;
	With thionyl chloride
	With thionyl chloride
	With hydrogenchloride at 20℃;
	With thionyl chloride at 20℃;
	With thionyl chloride
	With thionyl chloride at 20℃; Cooling;
	With thionyl chloride
	With thionyl chloride
	With thionyl chloride In tetrahydrofuran at 0℃; for 4.75h; Reflux;
	With thionyl chloride Inert atmosphere;
	With thionyl chloride at 0 - 70℃; for 18h;	126.e e) (S)-Methyl 2-amino-2-phenylacetate hydrochloride To a suspension of (S)-2-amino-2-phenylacetic acid (10 g, 66.15 mmol) in anhydrous MeOH (150 mL) was slowly added SOCI2 (7.22 mL, 99.22 mmol) at 0 °C. Then the mixture was stirred for 18 h at 60-70 °C. The solvent was removed in vacuo to give the title compound (13 g) as a white solid, which was used to the next step without further purification.

Reference： [1]Chang, Zen-Yu; Coates, Robert M. [Journal of Organic Chemistry, 1990, vol. 55, # 11, p. 3475 - 3483]
[2]Mancilla, Teresa; Carrillo, Lourdes; Zamudio-Rivera, Luis S.; Beltran, Hiram I.; Farfan, Norberto [Organic Preparations and Procedures International, 2001, vol. 33, # 4, p. 341 - 349]
[3]Location in patent: experimental part Kristensen, Tor E.; Vestli, Kristian; Hansen, Finn K.; Hansen, Tore [European Journal of Organic Chemistry, 2009, # 30, p. 5185 - 5191]
[4]Current Patent Assignee: ABBVIE INC - US2006/9518, 2006, A1 Location in patent: Page/Page column 22
[5]Liu, Sha; Jing, Li; Yu, Zhu-Jun; Wu, Chengyong; Zheng, Yongxiang; Zhang, En; Chen, Qiang; Yu, Yamei; Guo, Li; Wu, Yong; Li, Guo-Bo [European Journal of Medicinal Chemistry, 2018, vol. 145, p. 649 - 660]
[6]Person, Domonique; le Corre, Maurice [Bulletin de la Societe Chimique de France, 1989, # 5, p. 673 - 676]
[7]Location in patent: experimental part Kudelko, Agnieszka; Zieliński, Wojciech [Tetrahedron, 2009, vol. 65, # 6, p. 1200 - 1206]
[8]Current Patent Assignee: SHANDONG UNIVERSITY - CN111848454, 2020, A Location in patent: Paragraph 0067-0070
[9]Zoete, M. C. de; Ouwehand, A. A.; Rantwijk, F. van; Sheldon, R. A. [Recueil des Travaux Chimiques des Pays-Bas, 1995, vol. 114, # 4-5, p. 171 - 174]
[10]Li, Gui-Long; Zhao, Gang [Organic Letters, 2006, vol. 8, # 4, p. 633 - 636]
[11]Schwieger; Unterhalt [Archiv der Pharmazie, 1992, vol. 325, # 11, p. 709 - 715]
[12]Wu, Shao-Yong; Hirashima, Akinori; Kuwano, Eiichi; Eto, Morifusa [Agricultural and Biological Chemistry, 1987, vol. 51, # 2, p. 537 - 548]
[13]Bendayan, Andree; Masotti, Henriette; Peiffer, Gilbert; Siv, Chhan; Faure, Robert [Journal of Organometallic Chemistry, 1987, vol. 326, p. 289 - 298]
[14]Dondoni; Perrone; Semola [Synthesis, 1995, # 2, p. 181 - 186]
[15]Paleo, M. Rita; Calaza, M. Isabel; Sardina, F. Javier [Journal of Organic Chemistry, 1997, vol. 62, # 20, p. 6862 - 6869]
[16]Takenaka, Yukiko; Tanahashi, Takao; Shintaku, Masashi; Sakai, Takeshi; Nagakura, Naotaka; Parida [Phytochemistry, 2000, vol. 55, # 3, p. 275 - 284]
[17]Chen, Chao; Hong, Liang; Xu, Zhao-Qing; Liu, Lei; Wang, Rui [Organic Letters, 2006, vol. 8, # 11, p. 2277 - 2280]
[18]Laurent, Sophie; Elst, Luce Vander; Vroman, Antoine; Muller, Robert N. [Helvetica Chimica Acta, 2007, vol. 90, # 3, p. 562 - 573]
[19]Noorduin, Wim L.; Izumi, Toshiko; Millemaggi, Alessia; Leeman, Michel; Meekes, Hugo; Van Enckevort, Willem J. P.; Kellogg, Richard M.; Kaptein, Bernard; Vlieg, Elias; Blackmond, Donna G. [Journal of the American Chemical Society, 2008, vol. 130, # 4, p. 1158 - 1159]
[20]Location in patent: scheme or table Sai Sudhir; Nasir Baig; Chandrasekaran, Srinivasan [European Journal of Organic Chemistry, 2008, # 14, p. 2423 - 2429] Location in patent: scheme or table Nasir Baig; Kanimozhi, Catherine K.; Sudhir, V. Sai; Chandrasekaran, Srinivasan [Synlett, 2009, # 8, p. 1227 - 1232]
[21]Yang, Ying-Quan; Zhao, Gang [Chemistry - A European Journal, 2008, vol. 14, # 35, p. 10888 - 10891]
[22]Location in patent: scheme or table Zhao, Zhigang; Xia, Zhenyang; Li, Xiaorui; Shi, Peiyu [Journal of Chemical Research, 2011, vol. 35, # 1, p. 47 - 50]
[23]Location in patent: body text Chen, Yu; Zhao, Zhi-Gang; Liu, Xing-Li; Shi, Zhi-Chuan [Letters in Organic Chemistry, 2011, vol. 8, # 3, p. 210 - 215]
[24]Xu, Junxing; Hu, Yulai; Huang, Danfeng; Wang, Ke-Hu; Xu, Changming; Niu, Teng [Advanced Synthesis and Catalysis, 2012, vol. 354, # 2-3, p. 515 - 526]
[25]Zhang, Weijie; Tang, Ruiren; Yu, Huirong; Gao, Shu [Applied Organometallic Chemistry, 2014, vol. 28, # 7, p. 545 - 551]
[26]Current Patent Assignee: EUROPEAN MOLECULAR BIOLOGY LABORATORY; SAVIRA PHARMACEUTICALS GMBH - WO2017/158151, 2017, A1 Location in patent: Page/Page column 217; 218

2
[ 15028-39-4 ]
[ 25163-98-8 ]
Bz-L-Leu-L-Phg-OCH₃ [ No CAS ]
Bz-D-Leu-L-Phg-OCH₃ [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 4161 - 4163

3
[ 24424-99-5 ]
[ 15028-39-4 ]
[ 143978-88-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethylamine In dichloromethane at 20℃; for 38h;
91%	Stage #1: L-2-phenylglycine methyl ester hydrochloride With potassium carbonate In water for 1h; Stage #2: di-<i>tert</i>-butyl dicarbonate With guanidine hydrochloride In ethanol at 35 - 40℃; for 0.25h;	2.5. General procedure for N-tert-butoxycarbonylation of aminoacid esters (Table 2, entries 13-15): General procedure: Amino acid ester hydrochlorides and K2CO3 were suspended in water and stirred for one hour. The free amino acid esters were extracted with CH2Cl2 and dried with MgSO4. Evaporation of CH2Cl2 under reduced pressure gives free amino acid ester which should be immediately used for N-Boc protection. The free amino acid esters (1 mmol) in 1mL ethanol was added to a solution of di-tert-butyl dicarbonate (1.2 mmol) and guanidine hydrochloride (15 mol%) in ethanol (1 mL) at 35-40 °C and stirred for appropriate time. The work up was similar to same procedure for amines.
90%	Stage #1: L-2-phenylglycine methyl ester hydrochloride With triethylamine In tetrahydrofuran for 0.333333h; Cooling; Stage #2: di-<i>tert</i>-butyl dicarbonate In tetrahydrofuran at 20℃; for 24h;

	In 1,4-dioxane for 18h; Ambient temperature; Yield given;
	With triethylamine In methanol at 0 - 18℃; for 2h;	126.f f)(S)-Methyl 2-((tert-butoxycarbonyl)amino)-2-phenylacetate To a solution of (S)-methyl 2-amino-2-phenylacetate hydrochloride (13 g, 66.2 mmol) in MeOH (300 mL) was slowly added TEA (36.8 mL, 264.8 mmol) and Boc20 ( 8 g, 82.8 mmol) at 0 °C. Then the mixture was stirred for 2 h at 8-18 °C. The solvent was removed in vacuo and the residue was dissolved with EA (500 mL), the organic layer was washed with 10% aq. citric acid (100 mL), brine (100 mL), and dried over Na2S04. After filtration, the filtrate was concentrated in vacuo to give the crude product, which was triturated with PE/EA = 50/1 to give the title compound (15.5 g) as a white solid, which was used in the next step without further purification

Reference： [1]Li, Gui-Long; Zhao, Gang [Organic Letters, 2006, vol. 8, # 4, p. 633 - 636]
[2]Jahani, Fatemeh; Tajbakhsh, Mahmood; Golchoubian, Hamid; Khaksar, Samad [Tetrahedron Letters, 2011, vol. 52, # 12, p. 1260 - 1264]
[3]Location in patent: experimental part Kudelko, Agnieszka; Zieliński, Wojciech [Tetrahedron, 2009, vol. 65, # 6, p. 1200 - 1206]
[4]Dondoni; Perrone; Semola [Synthesis, 1995, # 2, p. 181 - 186]
[5]Current Patent Assignee: EUROPEAN MOLECULAR BIOLOGY LABORATORY; SAVIRA PHARMACEUTICALS GMBH - WO2017/158151, 2017, A1 Location in patent: Page/Page column 218

4
[ 15028-39-4 ]
(R)-2-Methoxy-2-phenethyl-pentanoic acid [ No CAS ]
(S)-((R)-2-Methoxy-2-phenethyl-pentanoylamino)-phenyl-acetic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol In N,N-dimethyl-formamide at 40℃; for 3h;

Reference： [1]Nakamura; Hirai; Sogi; Nakamura [Journal of the American Chemical Society, 1998, vol. 120, # 23, p. 5846 - 5847]

5
[ 15028-39-4 ]
[ 98-59-9 ]
[ 111047-54-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	With triethylamine In dichloromethane at 20℃; for 12h;
86%	With triethylamine In tetrahydrofuran at 20℃; for 16h;
	With triethylamine In dichloromethane cooling;

Reference： [1]Ordonez, Mario; De La Cruz-Cordero, Ricardo; Fernandez-Zertuche, Mario; Angel Munoz-Hernandez, Miguel; Garcia-Barradas, Oscar [Tetrahedron Asymmetry, 2004, vol. 15, # 19, p. 3035 - 3043]
[2]Wallace; Goodman; Kennedy; Davies; Cowden; Ashwood; Cottrell; Dolling; Reider [Organic letters, 2001, vol. 3, # 5, p. 671 - 674]
[3]Mastalerz, Harold; Gavai, Ashvinikumar V.; Fink, Brian; Struzynski, Charles; Tarrant, James; Vite, Gregory D.; Wong, Tai W.; Zhang, Guifen; Vyas, Dolatrai M. [Canadian Journal of Chemistry, 2006, vol. 84, # 4, p. 528 - 533]

6
[ 15028-39-4 ]
[ 587885-51-6 ]
(R)-Phenyl-(3,3,3-trifluoro-2-[((S)-methoxycarbonyl-phenyl-methyl)-amino]-methyl}-propionylamino)-acetic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With 1,4-diaza-bicyclo[2.2.2]octane In tetrachloromethane at 20℃; for 2h;

Reference： [1]Sani, Monica; Bruche, Luca; Chiva, Gema; Fustero, Santos; Piera, Julio; Volonterio, Alessandro; Zanda, Matteo [Angewandte Chemie - International Edition, 2003, vol. 42, # 18, p. 2060 - 2063]

7
[ 124-38-9 ]
[ 544-97-8 ]
[ 15028-39-4 ]
[ 463305-00-2 ]
(3R,4S)-3-((E)-But-1-enyl)-4-{(S)-1-[((S)-methoxycarbonyl-phenyl-methyl)-carbamoyl]-allyl}-cyclopentane-1,1-dicarboxylic acid dimethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: carbon dioxide; dimethyl zinc(II); dimethyl di(2,4-pentadienyl)propanedioate With bis(acetylacetonate)nickel(II); (S)-MEO-MOP In tetrahydrofuran; hexane at 20℃; for 42h; Stage #2: L-2-phenylglycine methyl ester hydrochloride With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0℃; for 1h;