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Quality Control of [ 102774-86-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 102774-86-7 ]

CAS No. :	102774-86-7	MDL No. :
Formula :	C₁₉H₁₅NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	321.33	Pubchem ID :	-
Synonyms :

Safety of [ 102774-86-7 ]

Signal Word:		Class:
Precautionary Statements:		UN#:
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Application In Synthesis of [ 102774-86-7 ]

* 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 [ 102774-86-7 ]
Downstream synthetic route of [ 102774-86-7 ]

[ 102774-86-7 ] Synthesis Path-Upstream 1~29

1
[ 6066-82-6 ]
[ 28920-43-6 ]
[ 74124-79-1 ]
[ 102774-86-7 ]

Yield	Reaction Conditions	Operation in experiment
95 kg	With tributyl-amine In tetrahydrofuran at -2 - 5℃; Large scale	From the reactor solid feed port one - time investment HosuL43. 8Kg (l. 25KmOl),With stirring,So that the kettle liquid at -2 ° C ~ 0 ° C.The tributylamine300Kg (l. 62 kP)And tetrahydrofuran450Kg into the high slot,After mixing,In 10 ~ llhr slowly added to the reactor in the reaction,The amount of added per hour for the 50 ~ 57Kg;And keep the kettle temperature not to exceed 5 ° C,Because of the exothermic reaction,After adding tributylamine in tetrahydrofuran solution,The reaction vessel was allowed to warm to room temperature and the reaction was continued for 7.5 h.A large amount of white solid crystals were observed to be precipitated by DSC from the reaction vessel.(3) filtered DSC crude: the reactor material in lhr evenly introduced into a fully enclosed centrifuge in N2Under the protection of throwing dry, and then twice the introduction of about 0 ° C tetrahydrofuran solvent 100Kg in the centrifuge rinse, throw dry,The DSC wet goods 120Kg. The wet goods in a vacuum oven at 40 ~ 45 ° C drying 7 ~ 8hr to constant weight, get out of the white crystalline powder 95Kg; HPLC analysis of 99. 1percent. The resulting filtrate was centrifuged to proceed to the next step. (3) filtered to obtain DSC crude: the reactor material in 1hr evenly introduced into a fully enclosed centrifuge, in the N₂Under the protection of throwing dry, and then twice the introduction of about 0 ° C tetrahydrofuran solvent 100Kg in the centrifuge rinse, throw dry, get DSC wet goods 120Kg.The wet product in a vacuum oven at 40 ~ 45 dry 7 ~ 8hr to constant weight, get out of the white crystalline powder 95Kg; HPLC analysis of 99.1percent.The resulting filtrate was centrifuged to proceed to the next step.(4) The centrifugal filtrate in step (3) is combined with two washing solvents and introduced into a 2000L distilling apparatus. The tetrahydrofuran solvent is removed at a vacuum control temperature of 0 to 5 DEG C, and the inside temperature of the kettle is kept at 40 to 42 DEG C .After the tetrahydrofuran was removed, 230 kg of dichloroethane was introduced, stirred at 40-50 ° C for 0.5 hr, and washed with 160 kg of water 3 times. The phases were separated and the dichloromethane was introduced into a 500 L autoclave.

Reference： [1] Patent: CN104030962, 2016, B, . Location in patent: Paragraph 0036-0041

2
[ 61-90-5 ]
[ 102774-86-7 ]
[ 35661-60-0 ]

Reference： [1] Liebigs Annalen der Chemie, 1988, p. 1095 - 1098

3
[ 56-86-0 ]
[ 102774-86-7 ]
[ 115-11-7 ]
[ 84793-07-7 ]
[ 71989-18-9 ]
[ 129460-14-6 ]

Reference： [1] Synthesis, 1990, # 7, p. 571 - 572

4
[ 18822-58-7 ]
[ 102774-86-7 ]
[ 71989-33-8 ]

Reference： [1] Liebigs Annalen der Chemie, 1988, p. 1095 - 1098

5
[ 56-84-8 ]
[ 102774-86-7 ]
[ 136083-57-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium carbonate In water; N,N-dimethyl-formamide at 0 - 20℃; for 1 h;	3.03 g (22.8 mmol; 1.2 eq.) of L-aspartic acid (Fluka) are dissolved in 54 ml (68.8 mmol; 3.6 eq.) of a 13.5percent (m/v) aqueous sodium carbonate solution, in a dry 250 ml round-bottomed flask. The medium is cooled in an ice bath at 0° C., then a solution of 6.41 g (19.0 mmol; 1 eq.) of N-(9-fluorenylmethoxycarbonyloxy)succinimide (N-Fmoc) dissolved in 44 ml of DMF is added with vigorous stirring (a precipitate forms in the reaction medium). The stirring is maintained for 1 hour at ambient temperature. The mixture is then diluted in 665 ml of water, and extracted with ether (180 ml) then with ethyl acetate (260 ml). The resulting aqueous phase is cooled in an ice bath and acidified to pH 2 with concentrated (6 N) hydrochloric acid. The aqueous phase containing the precipitated product (in the form of an oil) is extracted with ethyl acetate (660 ml). The organic phase derived from the extraction is washed with a saturated aqueous sodium chloride solution (335 ml), and then with water (2*35 ml), dried over sodium sulphate, and concentrated in a rotary evaporator (35° C.) until a small residual volume is obtained. Compound 17 is recrystallized by adding petroleum ether (approximately 10 times the residual volume) with vigorous stirring. After having allowed the mixture to separate by settling out for 2 hours at 4° C., the precipitate is filtered off and then dried for 24 hours in a vacuum oven. 6.22 g (17.5 mmol) of compound 17 are isolated in the form of a fine white powder. Empirical formula: C₁₉H₁₇NO₆, M=355.35 g.mol^-1 Yield: 92percent M.p.: 181° C. TLC: R_f=0.8 eluent: 60percent AcOH/BuOH 4/6 (v/v) ESI-MS +: m/z measured at 378.1 [M+Na]⁺, calculated at 378.1 for C₁₉H₁₇NO₆Na ¹H NMR (dmso-d₆, 500.13 MHz) δ (ppm): 12.60 (broad s, 2H, COOH); 7.89 (d, 2H, H-4/H-4', ³J_4-3=³J_4'-3'=7.5 Hz); 7.72 (d, 1H, N_αH); 7.70 (d, 2H, H-1/H-1', ³J_1-2=³J_1'-2'=7.5 Hz); 7.42 (t, 2H, H-3/H-3', ³J_3-2=³J_3-4=³J_3'-2'=³J_3'-4'=7.5 Hz); 7.33 (t, 2H, H-2/H-2', ³J_2-1=³J_2-3=³J_2'-1'=³J_2'-3'=7.5 Hz); 4.34 (m, 1H, H-α); 4.29 (d, 2H, H-8); 4.22 (t, 1H, H-7); 2.73 (dd, 1H, H-β,³J_β-α=5.5 Hz, ³J_β-β'=16.4 Hz); 2.58 (dd, 1H, H-β', ³J_β'-α=8.3 Hz, ³J=16.4 Hz) ¹³C NMR (dmso-d₆, 125.77 MHz) δ (ppm): 172.8, 171.8 (C_αH-COOH, C_βH₂-COOH); 155.9 (C-9); 143.9 (C-5/C-5'); 140.8 (C-6/C-6'); 127.7 (C-3/C-3'); 127.2 (C-2/C-2'); 125.4 (C-1/C-1'); 120.2 (C-4/C-4'); 65.8 (C-8); 50.6 (C-α); 46.7 (C-7); 36.1 (C-β)

Reference： [1] Patent: US2007/142324, 2007, A1, . Location in patent: Page/Page column 8

6
[ 102774-86-7 ]
[ 3057-74-7 ]
[ 71989-14-5 ]

Reference： [1] Liebigs Annalen der Chemie, 1988, p. 1095 - 1098

7
[ 56-84-8 ]
[ 102774-86-7 ]
[ 115-11-7 ]
[ 71989-14-5 ]
[ 129460-17-9 ]
[ 129460-09-9 ]

Reference： [1] Synthesis, 1990, # 7, p. 571 - 572

8
[ 2419-56-9 ]
[ 102774-86-7 ]
[ 71989-18-9 ]

Reference： [1] Liebigs Annalen der Chemie, 1988, p. 1095 - 1098

9
[ 56-86-0 ]
[ 102774-86-7 ]
[ 115-11-7 ]
[ 84793-07-7 ]
[ 71989-18-9 ]
[ 129460-14-6 ]

Reference： [1] Synthesis, 1990, # 7, p. 571 - 572

10
[ 56-84-8 ]
[ 102774-86-7 ]
[ 115-11-7 ]
[ 71989-14-5 ]
[ 129460-17-9 ]
[ 129460-09-9 ]

Reference： [1] Synthesis, 1990, # 7, p. 571 - 572

11
[ 73-32-5 ]
[ 102774-86-7 ]
[ 71989-23-6 ]

Reference： [1] Liebigs Annalen der Chemie, 1988, p. 1095 - 1098

12
[ 4378-13-6 ]
[ 102774-86-7 ]
[ 71989-35-0 ]

Reference： [1] Liebigs Annalen der Chemie, 1988, p. 1095 - 1098

13
[ 102774-86-7 ]
[ 3105-95-1 ]
[ 101555-63-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate In 1,4-dioxane at 20℃;	Synthesis of building blocks A Synthesis of (S)-1 -(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid A solution of the L-pipecolic acid (3.6g, 38.7 mmol) in 40ml of 10percent sodium carbonate was dissolved in round bottom flask and allowed to stir for 5 min at rt. To this solution was added F-moc succinamide (8.5g, 34.8 mmol) dissolved in 35 ml dioxane and the reaction was stirred overnight. After overnight stirring water was added and the aqueous layer was extracted with ethyl acetate. The aqueous layer was made acidic (pH-2) by addition of concentrated HCI. The acidic layer was extracted with ethyl acetate (3x 40ml). The organic phase was washed with 1 N HCI followed by brine, dried over MgSO₄ and concentrated under vacuo to yield a oily colorless liquid. The oily liquid was dissolved in ether and cooled to get fluffy white solid which was washed with hexane and dried to yield (S)-1 -(((9H-fluoren-9- yl)methoxy)carbonyl)piperidine-2-carboxylic acid ( 8.2g, 38.7mmol, 83percent). TLC (Hexane:EtOAc: TFA 1 : 1 : 0.2): RF = 0.60 HPLC (Gradient A) retention time= 24.6-24.8 min 1 H NMR (300 MHz, CDCI₃) 5=1 .28-1 .53 (m, 2H), 1 .69-1 .82 (m, 3H), 2.19-2.37 (m, 1 H), 3.15 (t, 1 H, J= 13.2Hz), 4.05-4.33 (m, 2H), 4.37-4.49 (m, 2H), 4.76-5.05(m, 1 H), 7.28-7.41 (m, 4H), 7.55-7.62 (m, 2H), 1 .77 (s, 2H). ¹³C NMR (75 MHz, CDCI₃) δ= 20.72, 24.70, 26.55, 41 .94, 47.25, 54.19, 67.86, 1 19.97, 125.08, 127.07, 127.68, 141 .33, 143.89, 156.65, 177.36 MS (ESI) m/z 352.66 [M + H] \ calculated 352.40 [M + H] ⁺.

Reference： [1] Patent: WO2013/91900, 2013, A1, . Location in patent: Page/Page column 41

14
[ 30845-10-4 ]
[ 102774-86-7 ]
[ 102971-73-3 ]

Reference： [1] Collection of Czechoslovak Chemical Communications, 2000, vol. 65, # 3, p. 407 - 424

15
[ 102774-86-7 ]
[ 60-32-2 ]
[ 88574-06-5 ]

Reference： [1] Helvetica Chimica Acta, 2000, vol. 83, # 6, p. 1268 - 1277

16
[ 102774-86-7 ]
[ 146549-21-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: With sodium hydrogencarbonate In water; acetone at 20℃; for 20 h; Stage #2: With hydrogenchloride In water; acetone	The allylglycine derivative 96 was prepared according to the procedure described by Paquet.²³⁰ Fmoc-OSu (14.60 g, 43.3 mmol) was added to stirred solution of L-allylglycine (5.00 g, 43.5 mmol) and NaHCO₃ (18.20 g, 0.22 mol) in a mixture of acetone:water (200 mL). The resultant white suspension was stirred at room temperature and after 20 h, t.l.c. analysis (SiO₂, light petroleum:EtOAc; 1:1) showed the absence of starting material. The reaction mixture was acidified with concentrated HCl (pH 2) and the acetone was removed under reduced pressure. The resultant suspension was extracted into DCM (375 mL) and the combined organic extract was washed with dilute HCl solution (1 M, 250 mL), water (2*50 mL), dried (MgSO₄) and evaporated under reduced pressure to afford the titled Fmoc-amino acid 96 as a colourless solid (14.01 g, 96percent), m.p. 137-138° C. (lit.²⁶⁶ 134-136° C.). ν_max (KBr): 3484s, 3198s, 3085m, 2967m, 2923m, 1723s, 1644m, 1525s, 1478w, 1449s, 1396m, 1340m, 1233s, 1189s, 1099m, 1048s, 998w, 966w, 943m, 924w, 850m, 781m, 761s, 740m, 648w, 623m, 582m, 560w, 540m, 424w cm^-1. ¹H n.m.r. (400 MHz, CDCl₃): δ 2.52-2.70 (2.34-2.49) (m, 2H, H3), 4.23 (t, J=6.9 Hz, 1H, H9'), 4.42 (4.30) (d, J=6.9 Hz, 2H, CH₂O), 4.52 (m, 1H, H2), 5.13-5.23 (m, 2H, H5), 5.31 (5.87) (bd, J=7.8 Hz, 1H, NH), 5.75 (m, 1H, H4), 6.63 (bs, 1H, OH), 7.31 (td, J=7.4, 0.8 Hz, 2H, H2', 7'), 7.38 (t, J=7.4 Hz, 2H, H3', 6'), 7.52-7.63 (m, 2H, H1', 8'), 7.76 (d, J=7.5 Hz, 2H, H4', 5'), one exchangeable proton (OH) not observed. ¹³C n.m.r. (100 MHz, CDCl₃): δ 36.7 (C3), 47.5 (C9'), 53.4 (C2), 68.1 (CH₂O), 122.0 (C5), 120.1 (C2', 7'), 125.4 (C3', 6'), 127.9 (C1', 8'), 128.0 (C4', 5'), 131.1 (C4), 141.7 (C8'a, 9'a), 144.0 (C4'a, 4'b), 156.3 (OCONH), 176.4 (C1). Mass Spectrum (ESI+, MeOH): m/z 338.4 (M+H)⁺, C₂₀H₂₀NO₄ requires 338.1; 360.3 (M+Na)⁺, C₂₀H₁₉NNaO₄ requires 360.1. Spectroscopic data were in agreement with those reported in the literature.²⁶⁶

Reference： [1] Patent: US2007/197429, 2007, A1, . Location in patent: Page/Page column 74-75

17
[ 102774-86-7 ]
[ 146982-27-6 ]

Reference： [1] Synthetic Communications, 1993, vol. 23, # 1, p. 49 - 53

18
[ 102774-86-7 ]
[ 55878-47-2 ]
[ 115186-31-7 ]

Reference： [1] Journal of Organic Chemistry, 1997, vol. 62, # 18, p. 6199 - 6203

19
[ 102774-86-7 ]
[ 90495-99-1 ]
[ 141743-15-9 ]

Reference： [1] Chemistry - A European Journal, 2001, vol. 7, # 18, p. 3911 - 3925

20
[ 102774-86-7 ]
[ 183673-71-4 ]
[ 183673-66-7 ]

Reference： [1] Journal of Organic Chemistry, 1996, vol. 61, # 22, p. 7650 - 7651

21
[ 102774-86-7 ]
[ 145315-38-4 ]
[ 143824-77-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 4, p. 855 - 857

22
[ 2840-26-8 ]
[ 102774-86-7 ]
[ 256935-69-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 25, p. 4416 - 4430

23
[ 23235-01-0 ]
[ 102774-86-7 ]
[ 198561-07-8 ]

Reference： [1] Chemical Communications, 2011, vol. 47, # 9, p. 2589 - 2591
[2] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 10, p. 2008 - 2018

24
[ 102774-86-7 ]
[ 851909-08-5 ]

Reference： [1] Chemistry - A European Journal, 2018, vol. 24, # 36, p. 9136 - 9147

25
[ 5817-22-1 ]
[ 102774-86-7 ]
[ 940301-35-9 ]

Reference： [1] Organic Letters, 2015, vol. 17, # 3, p. 492 - 495

26
[ 195071-49-9 ]
[ 102774-86-7 ]
[ 437655-95-3 ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: With potassium carbonate In water at 20℃; for 0.25 h; Stage #2: for 24 h;	L1 (0.79 g, 3.14 mmol) and K₂CO₃(1.04 g, 7.50 mmol) were dissolved in 5.8 mL of water and stirred at room temperature for 15 minutes after which N-(9-fluorenylmethoxycarbonyl) succinimide (Fmoc-OSu, 1.28 g, 3.79 mmol) was added and the mixture was stirred for 24 hours, while the progress of the reaction was monitored by TLC (CHCl₃/MeOH/AcOH, 5:1:0.06). The salt was filtered and the filtrate was washed with Et₂O, acidified to pH 1 using 3 N HCl, and the desired compound extracted with DCM. After removing the solvent in vacuo, Purification by RP-HPLC, the product-containing fraction was lyophilized to give Compound 11a (1.08 g, yield 73percent). Chemical formula of Compound 11a: C₂₅H₁NO₈required [M+H]⁺=474.2, found [M+H]⁺=474.9, [M+Na]⁺=496.9.

Reference： [1] Patent: US2018/169262, 2018, A1, . Location in patent: Paragraph 0181-0183

27
[ 102774-86-7 ]
[ 16626-02-1 ]
[ 908846-88-8 ]

Reference： [1] Tetrahedron Letters, 2008, vol. 49, # 17, p. 2795 - 2798

28
[ 102774-86-7 ]
[ 166734-64-1 ]
[ 856412-22-1 ]

Yield	Reaction Conditions	Operation in experiment
7.6 g	Stage #1: With edetate disodium; sodium carbonate In water for 0.166667 h; Stage #2: at -10 - 20℃; for 15 h;	General procedure: Complex 6 (6a, 6b, 6e, 6f) or 9 (3.5 mmol, 1.0 equiv.) was dissolved in MeOH (20 mL) and added dropwisely to 3 mol.L^-1 aqueous HCl (10.0 mL) at 70 over 5 minutes. The reaction mixture was refluxed and monitored by TLC. Upon completion, the reaction was cooled to room temperature and MeOH was removed by vacuo. The aqueous solution was washed with DCM for five times and combined organic layer was concentrated to recycle the chiral auxiliary. The aqueous layer which contained amino acid was thoroughly evaporated. The residue was treated with 6percent Na₂CO₃ solution to adjust the reaction pH to 9-10. EDTA·2Na (1.30 g, 3.5 mmol, 1.0 equiv.) was added to the aqueous solution and the reaction mixture was stirred for 10 min. Then Fmoc-OSu (1.30g, 3.85 mmol, 1.1 equiv.) in equal volume of acetonitrile was added into the reaction mixture dropwisely over 30 min in EtOH-ice bath (-10°C). The reaction was warmed to room temperature and left stirring for 15 h. Then the acetonitrile was removed in vacuo, the aqueous layers acidified to pH 1~2 with 1 M HCl. The aqueous fraction was then extracted with EtOAc, washed with brine, dried over sodium sulfate, and passed through a silica flash column with eluant of DCM/MeOH (100:1) to give the target compound as white solid.

Reference： [1] Tetrahedron Letters, 2017, vol. 58, # 24, p. 2374 - 2377

29
[ 1231709-27-5 ]
[ 102774-86-7 ]
[ 1198791-58-0 ]

Reference： [1] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 10, p. 2008 - 2018

[ 102774-86-7 ] Synthesis Path-Downstream 1~38

1
[ 2419-56-9 ]
[ 102774-86-7 ]
[ 71989-18-9 ]

Reference： [1]Liebigs Annalen der Chemie,1988,p. 1095 - 1098

2
[ 4378-13-6 ]
[ 102774-86-7 ]
[ 71989-35-0 ]

Reference： [1]Liebigs Annalen der Chemie,1988,p. 1095 - 1098

3
[ 18822-58-7 ]
[ 102774-86-7 ]
[ 71989-33-8 ]

Reference： [1]Liebigs Annalen der Chemie,1988,p. 1095 - 1098

4
[ 102774-86-7 ]
[ 15871-57-5 ]
[ 93372-25-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In water; acetonitrile

Reference： [1]Smythe, Mark L.; Nakaie, Clovis R.; Marshall, Garland R. [Journal of the American Chemical Society, 1995, vol. 117, # 42, p. 10555 - 10562]
[2]Elsaesser, Celine; Monien, Bernhard; Haehnel, Wolfgang; Bittl, Robert [Magnetic Resonance in Chemistry, 2005, vol. 43, # SPEC. ISS., p. S26-S33]

5
[ 102774-86-7 ]
[ 183673-71-4 ]
[ 183673-66-7 ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 7650 - 7651

6
[ 102774-86-7 ]
[ 55878-47-2 ]
[ 115186-31-7 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 6199 - 6203

7
[ 672-15-1 ]
[ 102774-86-7 ]
[ 172525-85-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1999,p. 3559 - 3564

8
[ 30845-10-4 ]
[ 102774-86-7 ]
[ 102971-73-3 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,2000,vol. 65,p. 407 - 424

9
[ 2041-14-7 ]
[ 102774-86-7 ]
[ 739356-33-3 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2000,vol. 19,p. 1787 - 1793

10
[ 2840-26-8 ]
[ 102774-86-7 ]
[ 256935-69-0 ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 4416 - 4430

11
[ 102774-86-7 ]
[ 145315-38-4 ]
[ 143824-77-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	With ethylenediaminetetraacetic acid; sodium hydrogencarbonate In acetone at 20℃;

Reference： [1]Schaschke, Norbert [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 4, p. 855 - 857]

12
[ 621-44-3 ]
[ 102774-86-7 ]
[ 136590-09-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3205 - 3208

13
[ 1404-90-6 ]
[ 102774-86-7 ]
C₈₁H₈₅Cl₂N₉O₂₆ [ No CAS ]
C₈₁H₈₅Cl₂N₉O₂₆ [ No CAS ]
C₉₆H₉₅Cl₂N₉O₂₈ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2325 - 2329

14
[ 102774-86-7 ]
[ 169396-92-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 665 - 670

15
[ 26905-03-3 ]
[ 102774-86-7 ]
[ 412332-08-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	In DMF (N,N-dimethyl-formamide) at 0℃; for 0.5h;	141.141B EXAMPLE 141B; 4-(4-Nitrophenyl)piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester Compound 141A (500 mg; 2.42 mmol) dissolved in DMF (18 ml) is treated at 0° C. with fmoc-succinimide (981 mg; 2.91 mmol) dissolved in DMF (10 ml).After stirring for 30 minutes at 0° C., the medium is diluted with dichloromethane and washed with water and with HCl solution (1 N).The organic phase is dried over MgSO4, filtered and evaporated to dryness.The syrup obtained is purifed by chromatography on a column of silica eluted with an 85/15 to 70/30 petroleum ether/ethyl acetate mixture.The pure product is obtained in the form of a pale yellow syrup (834 mg; 80%). 1H NMR, d6-DMSO (ppm): 1.30 m, 2H; 1.70 broad s, 2H; 2.85 m, 3H; 3.88 broad s, 1H; 4.07 broad s, 1H; 4.29 t, 1H; 4.40 broad s, 1H; 4.50 broad s, 1H; 7.35 t, 2H; 7.42 t, 2H; 7.50 d, 2H; 7.65 d, 2H; 7.86 d, 2H; 8.18 d, 2H. Mass spectrum (ESI): m/z 429 (MH+).

Reference： [1]Current Patent Assignee: PIERRE FABRE PARCIPATIONS - US2004/92524, 2004, A1 Location in patent: Page/Page column 39

16
[ 56-84-8 ]
[ 102774-86-7 ]
[ 136083-57-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium carbonate; In water; N,N-dimethyl-formamide; at 0 - 20℃; for 1h;	3.03 g (22.8 mmol; 1.2 eq.) of L-aspartic acid (Fluka) are dissolved in 54 ml (68.8 mmol; 3.6 eq.) of a 13.5% (m/v) aqueous sodium carbonate solution, in a dry 250 ml round-bottomed flask. The medium is cooled in an ice bath at 0 C., then a solution of 6.41 g (19.0 mmol; 1 eq.) of N-(9-fluorenylmethoxycarbonyloxy)succinimide (N-Fmoc) dissolved in 44 ml of DMF is added with vigorous stirring (a precipitate forms in the reaction medium). The stirring is maintained for 1 hour at ambient temperature. The mixture is then diluted in 665 ml of water, and extracted with ether (180 ml) then with ethyl acetate (260 ml). The resulting aqueous phase is cooled in an ice bath and acidified to pH 2 with concentrated (6 N) hydrochloric acid. The aqueous phase containing the precipitated product (in the form of an oil) is extracted with ethyl acetate (660 ml). The organic phase derived from the extraction is washed with a saturated aqueous sodium chloride solution (335 ml), and then with water (2*35 ml), dried over sodium sulphate, and concentrated in a rotary evaporator (35 C.) until a small residual volume is obtained. Compound 17 is recrystallized by adding petroleum ether (approximately 10 times the residual volume) with vigorous stirring. After having allowed the mixture to separate by settling out for 2 hours at 4 C., the precipitate is filtered off and then dried for 24 hours in a vacuum oven. 6.22 g (17.5 mmol) of compound 17 are isolated in the form of a fine white powder. Empirical formula: C19H17NO6, M=355.35 g.mol-1 Yield: 92% M.p.: 181 C. TLC: Rf=0.8 eluent: 60% AcOH/BuOH 4/6 (v/v) ESI-MS +: m/z measured at 378.1 [M+Na]+, calculated at 378.1 for C19H17NO6Na 1H NMR (dmso-d6, 500.13 MHz) delta (ppm): 12.60 (broad s, 2H, COOH); 7.89 (d, 2H, H-4/H-4', 3J4-3=3J4'-3'=7.5 Hz); 7.72 (d, 1H, NalphaH); 7.70 (d, 2H, H-1/H-1', 3J1-2=3J1'-2'=7.5 Hz); 7.42 (t, 2H, H-3/H-3', 3J3-2=3J3-4=3J3'-2'=3J3'-4'=7.5 Hz); 7.33 (t, 2H, H-2/H-2', 3J2-1=3J2-3=3J2'-1'=3J2'-3'=7.5 Hz); 4.34 (m, 1H, H-alpha); 4.29 (d, 2H, H-8); 4.22 (t, 1H, H-7); 2.73 (dd, 1H, H-beta,3Jbeta-alpha=5.5 Hz, 3Jbeta-beta'=16.4 Hz); 2.58 (dd, 1H, H-beta', 3Jbeta'-alpha=8.3 Hz, 3J=16.4 Hz) 13C NMR (dmso-d6, 125.77 MHz) delta (ppm): 172.8, 171.8 (CalphaH-COOH, CbetaH2-COOH); 155.9 (C-9); 143.9 (C-5/C-5'); 140.8 (C-6/C-6'); 127.7 (C-3/C-3'); 127.2 (C-2/C-2'); 125.4 (C-1/C-1'); 120.2 (C-4/C-4'); 65.8 (C-8); 50.6 (C-alpha); 46.7 (C-7); 36.1 (C-beta)

Reference： [1]Patent: US2007/142324,2007,A1 .Location in patent: Page/Page column 8

17
[ 102774-86-7 ]
[ 16626-02-1 ]
[ 908846-88-8 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 2795 - 2798

18
[ 102774-86-7 ]
[ 25197-96-0 ]
[ 460751-69-3 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 2795 - 2798

19
[ 102774-86-7 ]
L-tryptophanol [ No CAS ]
[ 153815-60-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hydrogencarbonate In water; acetone at 20℃; for 1h;

Reference： [1]Location in patent: experimental part Hossany, B. Rehana; Johnston, Blair D.; Wen, Xin; Borrelli, Silvia; Yuan, Yue; Johnson, Margaret A.; Pinto, B. Mario [Carbohydrate Research, 2009, vol. 344, # 12, p. 1412 - 1427]

20
[ 25456-86-4 ]
[ 102774-86-7 ]
Fmoc-Asp-OBu-t [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 3319 - 3330

21
[ 921-01-7 ]
[ 10419-77-9 ]
[ 102774-86-7 ]
3-(diethoxy-phosphorylmethylsulfanyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: D-cysteine; diethyl iodomethanephosphonate With sodium carbonate In 1,4-dioxane; water at 50℃; for 6h; Stage #2: 9-fluorenylmethyl N-succinimidyl carbonate In 1,4-dioxane; water at 0 - 20℃; for 12h;	3.A Cysteine (1.0 g, 8.3 mmol) was dissolved in a mixture of water (40 mL) and dioxane (10 mL). Iodomethyl-phosphonic acid diethyl ester (3.0 g, 11 mmol) and Na2C03 (2.0 g, 19 mmol) were added to the reaction mixture. After stirring for 6 h at 50 °C, the reaction mixture was cooled to 0 °C and a solution of carbonic acid 2, 5-dioxo-pyrrolidin-1-yl ester 9H-fluoren-9-ylmethyl ester (4.2 g, 12 mmol) in dioxane (16 mL) was added dropwise. The reaction was allowed to warm to room temperature. After stirring for 12 h, the reaction mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate (30 mL) and water (50 mL). The aqueous layer was extracted with ethyl acetate (2 x 30 mL), acidified with 6 M aqueous HCl to pH 1, and extracted with ethyl acetate (5 x 20 mL). The combined organic layers were dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by flash chromatography over silica gel (elution with DCM/ethyl acetate/acetic acid 90: 10: 5) to give the title compound as a colorless oil. MS (m/z): 494.2 [M+H+].

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2005/63259, 2005, A1 Location in patent: Page 64

22
[ 50428-03-0 ]
[ 102774-86-7 ]
[ 191215-87-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 5020 - 5027

23
[ 102774-86-7 ]
[ 2450-71-7 ]
[ 127896-08-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere;

Reference： [1]Leriche, Geoffray; Budin, Ghyslain; Brino, Laurent; Wagner, Alain [European Journal of Organic Chemistry, 2010, # 23, p. 4360 - 4364]

24
[ 23235-01-0 ]
[ 102774-86-7 ]
[ 198561-07-8 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 2589 - 2591
[2]Journal of Polymer Science, Part A: Polymer Chemistry,2012,vol. 50,p. 2008 - 2018

25
[ 1231709-27-5 ]
[ 102774-86-7 ]
[ 1198791-58-0 ]

Reference： [1]Journal of Polymer Science, Part A: Polymer Chemistry,2012,vol. 50,p. 2008 - 2018

26
[ 23235-01-0 ]
[ 102774-86-7 ]
[ 1063719-63-0 ]

Reference： [1]Journal of Polymer Science, Part A: Polymer Chemistry,2012,vol. 50,p. 2008 - 2018

27
[ 102774-86-7 ]
[ 3105-95-1 ]
[ 101555-63-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate; In 1,4-dioxane; at 20℃;	Synthesis of building blocks A Synthesis of (S)-1 -(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid A solution of the L-pipecolic acid (3.6g, 38.7 mmol) in 40ml of 10percent sodium carbonate was dissolved in round bottom flask and allowed to stir for 5 min at rt. To this solution was added F-moc succinamide (8.5g, 34.8 mmol) dissolved in 35 ml dioxane and the reaction was stirred overnight. After overnight stirring water was added and the aqueous layer was extracted with ethyl acetate. The aqueous layer was made acidic (pH-2) by addition of concentrated HCI. The acidic layer was extracted with ethyl acetate (3x 40ml). The organic phase was washed with 1 N HCI followed by brine, dried over MgSO4 and concentrated under vacuo to yield a oily colorless liquid. The oily liquid was dissolved in ether and cooled to get fluffy white solid which was washed with hexane and dried to yield (S)-1 -(((9H-fluoren-9- yl)methoxy)carbonyl)piperidine-2-carboxylic acid ( 8.2g, 38.7mmol, 83percent). TLC (Hexane:EtOAc: TFA 1 : 1 : 0.2): RF = 0.60 HPLC (Gradient A) retention time= 24.6-24.8 min 1 H NMR (300 MHz, CDCI3) 5=1 .28-1 .53 (m, 2H), 1 .69-1 .82 (m, 3H), 2.19-2.37 (m, 1 H), 3.15 (t, 1 H, J= 13.2Hz), 4.05-4.33 (m, 2H), 4.37-4.49 (m, 2H), 4.76-5.05(m, 1 H), 7.28-7.41 (m, 4H), 7.55-7.62 (m, 2H), 1 .77 (s, 2H). 13C NMR (75 MHz, CDCI3) delta= 20.72, 24.70, 26.55, 41 .94, 47.25, 54.19, 67.86, 1 19.97, 125.08, 127.07, 127.68, 141 .33, 143.89, 156.65, 177.36 MS (ESI) m/z 352.66 [M + H] \ calculated 352.40 [M + H] +.

Reference： [1]Patent: WO2013/91900,2013,A1 .Location in patent: Page/Page column 41

28
[ 102774-86-7 ]
[ 660-88-8 ]
[ 123622-48-0 ]

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 5673 - 5682

29
[ 699-03-6 ]
[ 102774-86-7 ]
[ 1520080-32-3 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 358 - 361

30
[ 102774-86-7 ]
[ 109-76-2 ]
[ 166410-34-0 ]
N,N'-di-Fmoc-1,3-diaminopropane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol at 0℃; for 0.00833333h; Flow reactor;

Reference： [1]Jong, Thingsoon; Bradley, Mark [Organic Letters, 2015, vol. 17, # 3, p. 422 - 425]

31
[ 5817-22-1 ]
[ 102774-86-7 ]
[ 940301-35-9 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 492 - 495

32
[ 102774-86-7 ]
[ 1397-89-3 ]
C₆₂H₈₂N₂O₁₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A round bottom flask was charged with amphotericin B (1 g, ca. 1.082 mmol, 1 equiv.) and Fmoc-succinimide (0.55 g, 1.62 mmol, 1.5 equiv.) which were dissolved in a2:1 mixture of DMF:MeOH (33.8 mL) at room temperature. Pyridine (0.5 mL, 6.21 mmol,5.74 equiv.) was subsequently added and the reaction was stirred for 12 hours at room temperature. The reaction mixture was then poured into diethyl ether (1 .0 L). After stirring for 30 minutes, the resulting yellow precipitate was isolated via BUchner filtration using Whatman 50 filter paper to afford a yellow solid. The filter cake was dried on the filter for10 minutes and then stored under vacuum for one hour.

Reference： [1]Patent: WO2016/112260,2016,A1 .Location in patent: Page/Page column 35; 36

33
[ 102774-86-7 ]
[ 166734-64-1 ]
[ 856412-22-1 ]

Yield	Reaction Conditions	Operation in experiment
7.6 g		General procedure: Complex 6 (6a, 6b, 6e, 6f) or 9 (3.5 mmol, 1.0 equiv.) was dissolved in MeOH (20 mL) and added dropwisely to 3 mol.L-1 aqueous HCl (10.0 mL) at 70 over 5 minutes. The reaction mixture was refluxed and monitored by TLC. Upon completion, the reaction was cooled to room temperature and MeOH was removed by vacuo. The aqueous solution was washed with DCM for five times and combined organic layer was concentrated to recycle the chiral auxiliary. The aqueous layer which contained amino acid was thoroughly evaporated. The residue was treated with 6% Na2CO3 solution to adjust the reaction pH to 9-10. EDTA·2Na (1.30 g, 3.5 mmol, 1.0 equiv.) was added to the aqueous solution and the reaction mixture was stirred for 10 min. Then Fmoc-OSu (1.30g, 3.85 mmol, 1.1 equiv.) in equal volume of acetonitrile was added into the reaction mixture dropwisely over 30 min in EtOH-ice bath (-10C). The reaction was warmed to room temperature and left stirring for 15 h. Then the acetonitrile was removed in vacuo, the aqueous layers acidified to pH 1~2 with 1 M HCl. The aqueous fraction was then extracted with EtOAc, washed with brine, dried over sodium sulfate, and passed through a silica flash column with eluant of DCM/MeOH (100:1) to give the target compound as white solid.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 2374 - 2377

34
C₃₁H₃₁N₃NiO₃ [ No CAS ]
[ 102774-86-7 ]
[ 851909-08-5 ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 9136 - 9147

35
[ 195071-49-9 ]
[ 102774-86-7 ]
[ 437655-95-3 ]

Yield	Reaction Conditions	Operation in experiment
73%		L1 (0.79 g, 3.14 mmol) and K2CO3 (1.04 g, 7.50 mmol) were dissolved in 5.8 mL of water and stirred at room temperature for 15 minutes after which N-(9-fluorenylmethoxycarbonyl) succinimide (Fmoc-OSu, 1.28 g, 3.79 mmol) was added and the mixture was stirred for 24 hours, while the progress of the reaction was monitored by TLC (CHCl3/MeOH/AcOH, 5:1:0.06). The salt was filtered and the filtrate was washed with Et2O, acidified to pH 1 using 3 N HCl, and the desired compound extracted with DCM. After removing the solvent in vacuo, Purification by RP-HPLC, the product-containing fraction was lyophilized to give Compound 11a (1.08 g, yield 73%). Chemical formula of Compound 11a: C25H1NO8 required [M+H]+=474.2, found [M+H]+=474.9, [M+Na]+=496.9.

Reference： [1]Patent: US2018/169262,2018,A1 .Location in patent: Paragraph 0181-0183

36
[ 498-40-8 ]
[ 102774-86-7 ]
(R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-sulfopropanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In 1,4-dioxane;Heating;	<strong>[498-40-8]L-<strong>[498-40-8]Cysteic acid</strong></strong> (500 mg, 2.95 mmol) was suspended in a mixture of 10% aqueous Na2CO3 (17.5 mL) and 1,4-dioxane (7.5 mL) and cooled in an ice bath. N-fluorenylmethoxycarbonyl succinimide (1.19 g, 3.54 mmol) was dissolved in 1,4-dioxane (12.5 mL) by gentle heating and the solution was added over 30 min via a dropping funnel with efficient stirring. The reaction mixture was stirred overnight and the organic solvent was removed in vacuo. The suspension was diluted with H2O (10 mL), washed with tert-butyl methyl ether (2×10 mL) and the aqueous phase was acidified with conc. HCl to pH 3.0. The solution was lyophilized to give 1.02 g of fmoc-cysteic-acid as white hygroscopic solid. This solid was used without further purification. Chemical Formula: C18H17NO7S, calculated [M-H]+:390.06, found [M-H]+=390.07.

Reference： [1]Patent: US2019/2484,2019,A1 .Location in patent: Paragraph 0419; 0422

37
[ 138146-22-2 ]
[ 102774-86-7 ]
[ 1310680-24-0 ]

Yield	Reaction Conditions	Operation in experiment
74%	With sodium hydrogencarbonate In 1,4-dioxane; water at 0 - 20℃;

Reference： [1]Debnath, Swapna; Ghosh, Suvankar; Pandit, Gopal; Satpati, Priyadarshi; Chatterjee, Sunanda [Journal of Organic Chemistry, 2021, vol. 86, # 17, p. 11310 - 11323]

38
[ 21820-51-9 ]
[ 102774-86-7 ]
[ 147762-53-6 ]

Yield	Reaction Conditions	Operation in experiment
	In lithium hydroxide monohydrate; acetonitrile at 20℃;

Reference： [1]Gao, Jie; Li, Xinxin; Shi, Yang; Wang, Youzhi; Yang, Zhimou; Zhang, Yiming [Journal of Materials Chemistry B, 2022, vol. 10, # 17, p. 3242 - 3247]

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H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 102774-86-7 ] {[proInfo.proName]}

Quality Control of [ 102774-86-7 ]

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[ 102774-86-7 ] Synthesis Path-Upstream 1~29

[ 102774-86-7 ] Synthesis Path-Downstream 1~38

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