3684-12-6|2-Phenyl-2-(phenylamino)acetic acid| Ambeed

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Quality Control of [ 3684-12-6 ] Purity: 97% SDS Specification

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NMR

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Product Details of [ 3684-12-6 ]

CAS No. :	3684-12-6
Formula :	C₁₄H₁₃NO₂
M.W :	227.26
SMILES Code :	O=C(O)C(NC1=CC=CC=C1)C2=CC=CC=C2
MDL No. :	MFCD01724775
InChI Key :	NFEVMRNCAGDLBK-UHFFFAOYSA-N
Pubchem ID :	19375

Safety of [ 3684-12-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 3684-12-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 3684-12-6 ]
Downstream synthetic route of [ 3684-12-6 ]

[ 3684-12-6 ] Synthesis Path-Upstream 1~1

1
[ 15727-49-8 ]
[ 3684-12-6 ]
[ 27356-66-7 ]
[ 1026-05-7 ]

References: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 9, p. 1754 - 1760.

[ 3684-12-6 ] Synthesis Path-Downstream 1~35

1
[ 13328-69-3 ]
[ 3684-12-6 ]
[ 13328-72-8 ]

References: [1]Journal of the American Chemical Society,1968,vol. 90,p. 7255 - 7261.

2
[ 3684-12-6 ]
[ 684-16-2 ]
[ 57750-04-6 ]

References: [1]Justus Liebigs Annalen der Chemie,1978,p. 1037 - 1051.

3
[ 3684-12-6 ]
[ 52827-05-1 ]

References: [1]Journal of Organic Chemistry,1974,vol. 39,p. 3676 - 3679.
[2]Chemische Berichte,1988,vol. 121,p. 95 - 104.

4
[ 124-38-9 ]
[ 538-51-2 ]
[ 3684-12-6 ]

References: [1]Gazzetta Chimica Italiana,1988,vol. 118,p. 643 - 648.
[2]Chemical Communications,2013,vol. 49,p. 5040 - 5042.

5
[ 124-38-9 ]
[ 538-51-2 ]
[ 758640-21-0 ]
[ 3684-12-6 ]

References: [1]Gazzetta Chimica Italiana,1988,vol. 118,p. 643 - 648.

6
[ 3684-12-6 ]
[ 95-54-5 ]
2-(α-phenylaminophenyl)benzimidazole [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1988,vol. 65,p. 67 - 68.

7
[ 3684-12-6 ]
[ 3815-83-6 ]

References: [1]Chemische Berichte,1988,vol. 121,p. 95 - 104.
[2]Journal of Organic Chemistry,1974,vol. 39,p. 3676 - 3679.

8
[ 100-52-7 ]
oxygen [ No CAS ]
[ 3684-12-6 ]

References: [1]Gazzetta Chimica Italiana,1988,vol. 118,p. 643 - 648.

9
[ 62-53-3 ]
ethane-α.β-bis-sulfonic acid chloride [ No CAS ]
[ 3684-12-6 ]

References: [1]Gazzetta Chimica Italiana,1988,vol. 118,p. 643 - 648.

10
[ 4553-59-7 ]
[ 3684-12-6 ]

References: [1]Chemische Berichte,1882,vol. 15,p. 2028.

11
[ 3684-12-6 ]
[ 57750-13-7 ]

References: [1]Justus Liebigs Annalen der Chemie,1978,p. 1037 - 1051.

12
C₂₃H₂₆N₂O₃ [ No CAS ]
[ 3684-12-6 ]

References: [1]Tetrahedron Letters,2008,vol. 49,p. 2099 - 2102.

13
[ 13314-52-8 ]
[ 3684-12-6 ]
[ 64548-94-3 ]

References: [1]Phosphorus, Sulfur and Silicon and the Related Elements,1990,vol. 53,p. 411 - 422.

14
[ 25179-00-4 ]
[ 3684-12-6 ]
(C₆H₅)(CH₃)GeN(C₆H₅)CH(C₆H₅)C(O)O [ No CAS ]

References: [1]Phosphorus, Sulfur and Silicon and the Related Elements,1990,vol. 53,p. 411 - 422.

15
[ 19065-49-7 ]
[ 3684-12-6 ]
[ 1233327-22-4 ]

Yield	Reaction Conditions	Operation in experiment
20%	With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20℃;Inert atmosphere;	A mixture of <strong>[3684-12-6]2-phenyl-2-(phenylamino)acetic acid</strong> (II) (175 mg, 0.77 mmol), DCC (192 mg, 0.92 mmol), HOBt (124 mg, 0.92 mmol) and 1-methyl- azepan-4-ol (100 mg, 0.77 mmol) in dry THF (100 mL) is stirred at RT overnight under nitrogen flowstream (UPLC-MS monitoring: complete conversion). The solvent is evaporated and the residue is taken up with aq. HCl and washed with EtOAc. The aqueous phase is basifed with NaHCO3 and extracted with DCM (three times). The organic layers are combined, dried over Na2SO4, filtered and evaporated to dryness. The resulting crude is first purified by flash chromatography (DCM to DCM/MeOH=95/5) and then by preparative LC-MS. The purified compound is partitioned between sat. NaHCO3 and DCM, the organic phase is dried over Na2SO4, filtered and evaporated under vacuum to give 53 mg of the title compound as brown oil (20% yield, mixture of diastereoisomers).1H NMR (300 MHz, CHLOROFORM-d) ppm: 12.76 (br. s., 1 H), 7.30 - 7.62 (m, 6 H), 7.07 - 7.23 (m, 2 H), 6.50 - 6.84 (m, 3 H), 5.15 - 5.39 (m, 1 H), 5.09 (d, 1 H), 3.21 - 3.79 (m, 2 H), 2.60 (d, 3 H), 1.80 - 3.15 (m, 8 H);LC-MS (ESI POS): 339.2 (MH+).

References: [1]Patent: WO2010/72338,2010,A1 .Location in patent: Page/Page column 120-121.

16
[ 3684-12-6 ]
[ 25333-42-0 ]
[ 1233329-45-7 ]
[ 1233329-46-8 ]

Yield	Reaction Conditions	Operation in experiment
28%; 14%		A solution of <strong>[3684-12-6]2-phenyl-2-(phenylamino)acetic acid</strong> (II) (1.90 g, 8.41 mmol) in dioxane, is added with with a 4M solution of HCl in dioxane (5 mL) and the reaction is stirred at RT for 1 h; the solvent is evaporated under reduced pressure to obtain a white solid which is dissolved in dry THF (40 mL). DCC (2.12 g, 10.0 mmol), HOBt (1.33 g, 10.0 mmol) and 3(R)-quinuclidinol (3.10 g, 25.1 mmol) are added to the resulting solution and the mixture is stirred for 96 h at RT under nitrogen flowstream (LC-MS monitoring: complete conversion). The solvent is evaporated, IN HCl (50 mL) is added to the resulting crude and the aqueous layer is washed with EtOAc (2x100 mL); a saturated solution Of NaHCO3 is added to the aqueous layer (pH=7- 8) and the desired compound is extracted with DCM. The resulting crude is purified by flash chromatography (DCM/MeOH=95/5, 0.1% NH3 (aq.)) recovering diastereoisomer 1 of C2 as a white solid (0.8 g; 28% yield, single diastereoisomer), and subsequently diastereoisomer 2 of C2 as a white solid (0.4 g, 14% yield, single diastereoisomer). Diastereoisomer 1 of C2 (80 mg) is further purified by preparativeLC-MS to obtain 55.3 mg of a pale yellow oil (TFA salt).Diastereoisomer 2 of C2 (65 mg) is further purified by preparative LC-MS to obtain 28.3 mg of a pale yellow oil (TFA salt).Diastereoisomer 1 of C2: 1H NMR (300 MHz, DMSO-d6) ppm: 9.38 (br. s., IH), 7.50 - 7.72 (m,2H), 7.26 - 7.50 (m, 3H), 6.98 - 7.25 (m, 2H), 6.68 - 6.83 (m, 2H), 6.52 - 6.68 (m, IH), 5.34 (s, IH), 4.92 - 5.18 (m, IH), 3.57 - 3.67 (m, IH), 3.05 - 3.33 (m, 3H), 2.57 - 2.81 (m, 2H), 2.08 - 2.30 (m, IH), 1.63 - 1.94 (m, 4H);LC-MS (ESI POS): 337.3 (MH+); [α]D= -32.0 (c=0.5, MeOH).Diastereoisomer 2 of C2:1H NMR (300 MHz, DMSO-d6) ppm: 9.49 (br. s., IH), 7.48 - 7.64 (m, 2H), 7.25 - 7.48 (m, 3H), 7.00 - 7.15 (m, 2H), 6.66 - 6.78 (m, 2H), 6.52 - 6.65 (m, IH), 5.30 (s, IH), 4.94 - 5.16 (m, IH), 3.54 - 3.76 (m, IH), 3.03 - 3.28 (m, 5H), 2.03 (br. s., IH), 1.65 - 1.93 (m, 2H), 1.33 - 1.65 (m, 2H);LC-MS (ESI POS): 337.3 (MH+);[α]D= 2.4 (c=0.5, MeOH).
22.5%; 13.7%	With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20℃; for 16h;	To a solution of <strong>[3684-12-6]2-phenyl-2-(phenylamino)acetic acid</strong> (II) (3.40 g, 14.9 mmol) in THF (600 ml), was added DCC (4.02 g, 19.4 mmol), HOBt (3.06 g, 19.4 mmol) and 3(R)-quinuclidinol (3.80 g, 29.9 mmol). The resulting mixture was stirred for 16 h at room temperature (UPLC-MS monitoring: complete conversion). The solvent was evaporated, the residue was taken up with EtOAc and the insoluble was eliminated by filtration. The clear solution was washed with 1M K2CO3 and then with brine, was dried over Na2SO4, filtered and evaporated to dryness. The resulting crude was purified by flash chromatography (DCM/MeOH=95/5, 0.1% NH3 (aq.)) recovering first diastereomer 1 of 12 as a white solid (1.13 g, 22.5% yield, single diastereomer), and subsequently diastereomer 2 of 12 (0.69 g, 13.7% yield, single diastereomer).Diastereomer 1 of 12:1H NMR (300 MHz, DMSO- 6) ppm: 7.48 - 7.59 (m, 2 H), 7.26 - 7.46 (m, 3 H), 7.02 - 7.14 (m, 2 H), 6.67 - 6.79 (m, 2 H), 6.51 - 6.64 (m, 1 H), 6.27 (d, 1 H), 5.26 (d, 1 H), 4.61 - 4.78 (m, 1 H), 2.96 (ddd, 1 H), 2.55 - 2.67 (m, 3 H), 2.16 - 2.37 (m, 1 H), 2.06 (d, 1 H), 1.79 - 1.94 (m, 1 H), 1.59 - 1.76 (m, 1 H), 1.35 - 1.59 (m, 2 H), 1.20 - 1.34 (m, 1 H);LC-MS (ESI POS): 337.04 (MH+).Diastereomer 2 of 12:1H NMR (300 MHz, DMSO- 6) ppm: 7.48 - 7.60 (m, 2 H), 7.24 - 7.43 (m,3 H), 6.97 - 7.14 (m, 2 H), 6.66 - 6.78 (m, 2 H), 6.51 - 6.66 (m, 1 H), 6.26 (d, 1 H), 5.24 (d, 1 H), 4.62 - 4.81 (m, 1 H), 3.08 (ddd, 1 H), 2.54 - 2.70 (m, 5 H), 1.64 - 1.79 (m, 1 H), 1.32 - 1.64 (m, 2 H), 1.16 - 1.32 (m, 1 H), 0.93 - 1.16 (m, 1 H);LC-MS (ESI POS): 337.04 (MH+).
22.5%; 13.7%	With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20℃; for 16h;	To a solution of <strong>[3684-12-6]2-phenyl-2-(phenylamino)acetic acid</strong> (II) (3.40 g, 14.9 mmol) in THF (600 ml), DCC (4.02 g, 19.4 mmol), HOBt (3.06 g, 19.44 mmol) and 3(R)-quinuclidinol (3.80 g, 29.9 mmol) were added. The resulting mixture was stirred for 16 h at room temperature (UPLC-MS monitoring: complete conversion). The solvent was evaporated, the residue was taken up with EtOAc and the insoluble was eliminated by filtration. The clear solution was washed with 1M K2CO3 and then with brine, dried over Na2SO4, filtered and evaporated to dryness. The resulting crude was purified by flash chromatography (DCM/MeOH=95/5, 0.1 % NH3 (aq.)) recovering first diastereomer 1 of 12 (1.13 g, 22.5% yield, single diastereomer), and subsequently diastereomer 2 of 12 (0.69 g, 13.7% yield, single diastereomer).Diastereomer 1 of 12:1H NMR (300 MHz, DMSO- 6) ppm: 7.48 - 7.59 (m, 2 H), 7.26 - 7.46 (m, 3 H), 7.02 - 7.14 (m, 2 H), 6.67 - 6.79 (m, 2 H), 6.51 - 6.64 (m, 1 H), 6.27 (d, 1 H), 5.26 (d, 1 H), 4.61 - 4.78 (m, 1 H), 2.96 (ddd, 1 H), 2.55 - 2.67 (m, 3 H), 2.16 - 2.37 (m, 1 H), 2.06 (d, 1 H), 1.79 - 1.94 (m, 1 H), 1.59 - 1.76 (m, 1 H), 1.35 - 1.59 (m, 2 H), 1.20 - 1.34 (m, 1 H);LC-MS (ESI POS): 337.04 (MH+);[cc]D= -44.6 (c=0.25 MeOH).Diastereomer 2 of 12:1H NMR (300 MHz, DMSO- 6) ppm: 7.48 - 7.60 (m, 2 H), 7.24 - 7.43 (m, 3 H), 6.97 - 7.14 (m, 2 H), 6.66 - 6.78 (m, 2 H), 6.51 - 6.66 (m, 1 H), 6.26 (d, 1 H), 5.24 (d, 1 H), 4.62 - 4.81 (m, 1 H), 3.08 (ddd, 1 H), 2.54 - 2.70 (m, 5 H), 1.64 - 1.79 (m, 1 H), 1.32 - 1.64 (m, 2 H), 1.16 - 1.32 (m, 1 H), 0.93 - 1.16 (m, 1 H);LC-MS (ESI POS): 337.04 (MH+);[cc]D= +27.6 (c= 0.25 MeOH).

References: [1]Patent: WO2010/72338,2010,A1 .Location in patent: Page/Page column 49-50.
[2]Patent: WO2011/160919,2011,A1 .Location in patent: Page/Page column 32-33.
[3]Patent: WO2011/161018,2011,A1 .Location in patent: Page/Page column 26-27.

17
[ 3684-12-6 ]
[ 25333-42-0 ]
[ 1233327-21-3 ]

Yield	Reaction Conditions	Operation in experiment
10%	With diethyl diazodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃;	A solution of <strong>[3684-12-6]2-phenyl-2-(phenylamino)acetic acid</strong> (II) (500 mg, 2.20 mmol), (R)-quinuclidin-3-ol (280 mg, 2.20 mmol) and triphenylphosphine (577 mg, 2.20 mmol) in dry THF (7 mL) cooled at 00C, is added with (E)-diethyl diazene-l,2-dicarboxylate (0.35 mL, 2.20 mmol) and the reaction is stirred 2h at RT. The solvent is removed under vacuum and the residue is taken up with EtOAc, washed with 5% NaHCO3 and brine, dried over Na2SO4 and evaporated to dryness. The resulting yellow oil is purified by flash chromatography (EtOAc/MeOH/NH4OH =90/10/0.1 to 70/30/0.1) to obtain desired product as a white powder (78.0 mg, 10% yield, mixture of diastereoisomer).1H NMR (300 MHz, DMSO-J6) ppmDiastereoisomer 1 of C106: 7.48 - 7.62 (m, 2 H), 7.24 - 7.45 (m, 3 H), 6.98 - 7.11 (m, 2 H), 6.66 - 6.75 (m, 2 H), 6.51 - 6.62 (m, 1 H), 6.27 (d, 1 H), 5.25 (d, 1 H), 4.58 - 4.82 (m, 1 H), 3.08 (dd, 1 H), 2.54 - 2.70 (m, 5 H), 1.62 - 1.75 (m, 1 H), 0.97 - 1.60 (m, 4 H);Diastereoisomer 2 of C106: 7.48 - 7.62 (m, 2 H), 7.24 - 7.45 (m, 3 H), 6.98 - 7.11 (m, 2 H), 6.66 - 6.75 (m, 2 H), 6.51 - 6.62 (m, 1 H), 6.27 (d, 1 H), 5.26 (d, 1 H), 4.58 - 4.82 (m, 1 H), 2.95 (m, 1 H), 2.54 - 2.70 (m, 4 H), 2.02 - 2.14 (m, 1 H), 1.86 - 1.95 (m, 1 H), 0.97 - 1.60 (m, 4 H);LC-MS (ESI POS): 337.2 (MH+).

References: [1]Patent: WO2010/72338,2010,A1 .Location in patent: Page/Page column 119-120.

18
[ 106-52-5 ]
[ 3684-12-6 ]
[ 1233326-73-2 ]

Yield	Reaction Conditions	Operation in experiment
7%		A solution of <strong>[3684-12-6]2-phenyl-2-(phenylamino)acetic acid</strong> (II) (234 mg, 0.91 mmol) in dioxane, is added with a 4M solution of HCl in dioxane (5 mL) and the reaction is stirred at RT for 1 h; the solvent is evaporated under reduced pressure to obtain a white solid which is dissolved in dry THF (10 mL). DCC (222 mg, 1.12 mmol), HOBt (144 mg, 1.14 mmol) and N-methyl-4-piperidinol (307 mg, 2.71 mmol) are added and the mixture is stirred for 96h at RT under nitrogen flowstream (LC-MS monitoring: complete conversion). The solvent is evaporated and the residue is partitioned between DCM and water; the organic layer is separated and dried over Na2SO4. The crude compound is purified by preparative LC-MS and the collected fractions are portioned between 2M K2CO3 and EtOAc. The 'organic phase is dried over Na2SO4, filtered and evaporated to dryness to obtain 20.6 mg of the title compound as a white solid (7% yield, racemic mixture).1H NMR (300 MHz, DMSO-d6) ppm: 7.45 - 7.60 (m, 2H), 7.20 - 7.45 (m, 3H), 6.95 - 7.17 (m, 2H), 6.69 (d, 2H), 6.47 - 6.63 (m, IH), 6.23 (d, IH), 5.20 (d, IH), 4.71 (tt, IH), 2.34 - 2.48 (m, IH), 2.11 - 2.25 (m, 2H), 2.09 (s, 3H), 1.94 - 2.08 (m, IH), 1.71 - 1.90 (m, IH), 1.51 - 1.71 (m, 2H), 1.29 - 1.51 (m, IH); LC-MS (ESI POS): 325.2 (MH+).

References: [1]Patent: WO2010/72338,2010,A1 .Location in patent: Page/Page column 58-59.

19
[ 3684-12-6 ]
3β-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane [ No CAS ]
8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenyl-2-(phenylamino)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 100℃; for 1h;microwave irradiation;	A mixture of <strong>[3684-12-6]2-phenyl-2-(phenylamino)acetic acid</strong> Il (250 mg, 0.90 mmol), EDC (255 mg, 1.35 mmol), HOBt (245 mg, 1.80 mmol) and 8-methyl-8-azabicyclo[3.2.1]octan-3-ol (380 mg, 2.71 mmol) in dry DMF (10 mL) is heated under microwave irradiation at 1000C for 1 h (LC-MS monitoring: complete conversion). The reaction is concentrated under reduced pressure and the residue is partitioned between EtOAc and water. The organic phase is dried over Na2SO4, filtered and evaporated to dryness. The resulting crude is purified by preparative HPLC. The collected compound is partitioned between IN NaHCO3 and DCM, the organic phase is separated dried over Na2SO4, filtered and evaporated under vacuum to give 20.1 mg of the title compound as a colorless oil (7% yield, mixture of diastereoisomers). II1iiH NMR (300 MHz, CHLOROFORM-d) ppm: 7.45 - 7.57 (m, 2 H), 7.29 - 7.45 (m, 3 H), 7.04 - 7.21 (m, 2 H), 6.65 - 6.77 (m, 1 H), 6.51 - 6.65 (m, 2 H), 5.02 - 5.13 (m, 2 H), 5.00 (d, 1 H), 3.07 - 3.30 (m, 1 H), 2.81 - 3.07 (m, 1 H), 2.28 (s, 3 H), 2.19 - 2.27 (m, 1 H), 1.84 - 2.18 (m, 3 H), 1.70 - 1.82 (m, 2 H), 1.45 (d, I H), 1.17 (ddd, 1 H);LC-MS (ESI POS): 351.3 (MH+).

References: [1]Patent: WO2010/72338,2010,A1 .Location in patent: Page/Page column 61-62.

20
[ 104641-60-3 ]
[ 3684-12-6 ]
[ 1233326-74-3 ]

Yield	Reaction Conditions	Operation in experiment
33%	With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20℃;Inert atmosphere;	A mixture of <strong>[3684-12-6]2-phenyl-2-(phenylamino)acetic acid</strong> (II) (200 mg, 0.88 mmol), DCC (218 mg, 1.05 mmol), HOBt (142 mg, 1.05 mmol) and (R)- I- methylpyrrolidin-3-ol (289 uL, 2.64 mmol) in dry THF (10 mL) is stirred at room temperature overnight under nitrogen flowstream (LC-MS monitoring: complete conversion). The solvent is evaporated and the residue is taken up with aq. HCl (pH about 2) and washed with DCM. The aqueous phase is basified with NaHCO3 and extracted with DCM (three times). The organic layers are combined, dried over Na2SO4, filtered and evaporated to dryness. The resulting crude is first purified by flash chromatography (DCM to DCM/MeOH=95/5) and then by preparative LC-MS. The purified compound is partitioned between sat. NaHCO3 and DCM, the organic phase is dried over Na2SO4, filtered and evaporated under vacuum to give 90.8 mg of the title compound as brown oil (33% yield, mixture of diastereoisomers).1H NMR (300 MHz, CHLOROFORM-d) ppmDiastereoisomer 1 of C 14: 7.46 - 7.57 (m, 2 H), 7.29 - 7.45 (m, 3 H), 7.08 - 7.21 (m, 2 H), 6.67 - 6.81 (m, 1 H), 6.50 - 6.67 (m, 2 H), 5.20 - 5.37 (m, 1 H), 5.12 (d, 1 H), 4.84 - 5.05 (m, 1 H), 2.46 - 3.04 (m, 4 H), 2.44 (s, 3 H), 2.10 - 2.26 (m, 1 H), 1.63 - 1.82 (m, 1 H). Diastereoisomer 2 of C14: 7.46 - 7.57 (m, 2 H), 7.29 - 7.45 (m, 3 H), 7.08 - 7.21 (m, 2 H), 6.67 - 6.81 (m, 1 H), 6.50 - 6.67 (m, 2 H), 5.20 - 5.37 (m, 1 H), 5.12 (d, 1 H), 4.84 - 5.05 (m, 1 H), 2.46 - 3.04 (m, 4 H), 2.33 (s, 3 H), 2.26 - 2.40 (m, 1 H), 1.86 - 2.05 (m, 1 H);LC-MS (ESI POS): 31 1.3 (MH+).
33%	With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20℃; for 40h;Inert atmosphere;	A mixture of <strong>[3684-12-6]2-phenyl-2-(phenylamino)acetic acid</strong> (II) (200 mg, 0.88 mmol), DCC (218 mg, 1.05 mmol), HOBt (142 mg, 1.05 mmol) and (R)-l- methylpyrrolidin-3-ol (289 uL, 2.64 mmol) in dry THF (10 mL) was stirred at room temperature overnight under nitrogen flowstream (LC-MS monitoring: complete conversion). The solvent was evaporated and the residue was taken up with aq. HCl (pH about 2) and washed with DCM. The aqueous phase was basified with NaHCO3 and extracted with DCM (three times). The organic layers were combined, dried over Na2SO4, filtered and evaporated to dryness. The resulting crude was first purified by flash chromatography (DCM to DCM/MeOH=95/5) and then by preparative LC-MS. The purified compound was partitioned between sat. NaHCO and DCM, the organic phase was dried over Na2SO4, filtered and evaporated under vacuum to give 90.8 mg of the title compound (33% yield, mixture of diastereomers).1H NMR (300 MHz, CHLOROFORM-d) ppmDiastereomer 1 of 133: 7.46 - 7.57 (m, 2 H), 7.29 - 7.45 (m, 3 H), 7.08 - 7.21 (m, 2 H), 6.67 - 6.81 (m, 1 H), 6.50 - 6.67 (m, 2 H), 5.20 - 5.37 (m, 1 H), 5.12 (d, 1 H), 4.84 - 5.05 (m, 1 H), 2.46 - 3.04 (m, 4 H), 2.44 (s, 3 H), 2.10 - 2.26 (m, 1 H), 1.63 - 1.82 (m, 1 H).Diastereomer 2 of 133: 7.46 - 7.57 (m, 2 H), 7.29 - 7.45 (m, 3 H), 7.08 - 7.21 (m, 2 H), 6.67 - 6.81 (m, 1 H), 6.50 - 6.67 (m, 2 H), 5.20 - 5.37 (m, 1 H), 5.12 (d, 1 H), 4.84 - 5.05 (m, 1 H), 2.46 - 3.04 (m, 4 H), 2.33 (s, 3 H), 2.26 - 2.40 (m, 1 H), 1.86 - 2.05 (m, 1 H);LC-MS (ESI POS): 31 1.3 (MH+).

References: [1]Patent: WO2010/72338,2010,A1 .Location in patent: Page/Page column 59-60.
[2]Patent: WO2011/160919,2011,A1 .Location in patent: Page/Page column 52-53.

21
[ 4870-65-9 ]
dichloromethane (DCM) [ No CAS ]
[ 3684-12-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sodium carbonate; In aniline;	Preparation of 2-phenyl-2-(phenylamino)acetic acid (I1) α-Bromophenylacetic acid (5.01 g, 23.2 mmol) was dissolved in aniline (25 ml, 274 mmol), and the mixture reacted in a closed vessel under microwave irradiation at 120 C. for 5 minutes (UPLC-MS monitoring: complete conversion). Dichloromethane (DCM) (100 ml) was added to the reaction mixture, and the resulting solid was filtered; 2M Na2CO3 (50 ml) was added to the solution, and the aqueous layer was washed with DCM (3*100 ml). The aqueous layer was acidified with 12N HCl (36 ml) and the title compound was recovered as racemic mixture by filtration (5.1 g, 97% yield).
97%	With sodium carbonate; In aniline;	Preparation of 2-phenyl-2-(phenylamino)acetic acid (I1) α-Bromophenylacetic acid (5.01 g, 23.2 mmol) was dissolved in aniline (25 ml, 274 mmol), and the mixture was reacted in a closed vessel under microwave irradiation at 120 C. for 5 minutes (UPLC-MS monitoring: complete conversion). Dichloromethane (DCM) (100 ml) was added to the reaction mixture, and the resulting solid was filtered; 2M Na2CO3 (50 ml) was added to the solution, and the aqueous layer was washed with DCM (3*100 ml). The aqueous layer was acidified with 12N HCl (36 ml) and the title compound was recovered as racemic mixture by filtration (5.1 g, 97% yield).

References: [1]Patent: US2011/311458,2011,A1 .
[2]Patent: US2011/311459,2011,A1 .

22
[ 3684-12-6 ]
[ 1352565-19-5 ]

References: [1]Patent: WO2011/160919,2011,A1 .

23
[ 3684-12-6 ]
[ 1352565-27-5 ]

References: [1]Patent: WO2011/160919,2011,A1 .

24
[ 3684-12-6 ]
[ 1352565-29-7 ]

References: [1]Patent: WO2011/160919,2011,A1 .

25
[ 3684-12-6 ]
[ 1352565-30-0 ]

References: [1]Patent: WO2011/160919,2011,A1 .

26
[ 3684-12-6 ]
[ 1352565-31-1 ]

References: [1]Patent: WO2011/160919,2011,A1 .

27
[ 3684-12-6 ]
[ 1352565-32-2 ]

References: [1]Patent: WO2011/160919,2011,A1 .

28
[ 3684-12-6 ]
[ 1352565-34-4 ]

References: [1]Patent: WO2011/160919,2011,A1 .

29
[ 3684-12-6 ]
[ 1233330-73-8 ]